A new approach to enantioselective cyanation of imines with Et2AlCN
Tetrahedron AsymmetryPublished 23 April 2004
Shuichi Nakamura, Naoki Sato, Masashige Sugimoto, Takeshi Toru
Citations113
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
An enantioselective Strecker-type reaction of imines with Et2AlCN in the presence of chiral additives has been examined. The enantioselectivity varied depending on the substituents of the imino group as well as the chiral additives used. Thus, α-aminonitriles were obtained in good yields with good enantioselectivities in the reaction of N-benzylidenebenzhydrylamine with Et2AlCN and BINOL. The reaction with excess BINOL gave the aminonitrile with reversed configuration.
Keywords
Chemistry
Chemical ReviewsCatalytic Enantioselective Addition to Imines
1,564 Citations1999Shū Kobayashi, Haruro Ishitani
Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
Journal of the American Chemical SocietyStructure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction
571 Citations2002Petr Váchal, Eric N. Jacobsen
Rational optimization of catalyst structure based on the mechanistic insight led to an improved catalyst for the asymmetric Strecker reaction.
Journal of the American Chemical SocietyAsymmetric Catalysis of the Strecker Amino Acid Synthesis by a Cyclic Dipeptide
339 Citations1996Mani S. Iyer, Kenneth M. Gigstad +2 more
Angewandte Chemie International EditionRecent Developments in Catalytic Asymmetric Strecker-Type Reactions
251 Citations2001Larry Yet
Journal of the American Chemical SocietyTi-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids
235 Citations1999Clinton A. Krueger, Kevin W. Kuntz +5 more
Journal of the American Chemical SocietyCatalytic Enantioselective Strecker Reaction of Ketoimines
208 Citations2003Shuji Masumoto, Hiroyuki Usuda +3 more
The reaction has a broad substrate generality, giving high enantioselectivity from aromatic, ethyl, primary alkyl, and alpha,beta-unsaturated ketoimines, and could be easily converted to disubstituted alpha-amino acids and their derivatives.
Journal of the American Chemical SocietyLanthanide(III)-Catalyzed Enantioselective Diels-Alder Reactions. Stereoselective Synthesis of Both Enantiomers by Using a Single Chiral Source and a Choice of Achiral Ligands
206 Citations1994Shu̅ Kobayashi, Haruro Ishitani
Angewandte Chemie International EditionA Catalytic Asymmetric Strecker-Type Reaction: Interesting Reactivity Difference between TMSCN and HCN
198 Citations2000Masahiro Takamura, Yoshitaka Hamashima +3 more
Angewandte Chemie International EditionCatalytic, Enantioselective Synthesis ofα-Aminonitriles with a Novel Zirconium Catalyst
160 Citations1998Haruro Ishitani, Susumu Komiyama +1 more
Strecker reactions of aldimines with Bu3 SnCN in the presence of the novel chiral zirconium binuclear catalyst 1 provide α-aminonitriles in good yields and with high enantioselectivities.
Angewandte Chemie International EditionThe First Enantioselective Aza-Diels-Alder Reactions of Imino Dienophiles on Use of a Chiral Zirconium Catalyst
150 Citations1998Shu̅ Kobayashi, Susumu Komiyama +1 more
Chiral dihydropyridone derivatives 3 are obtained in high yields and with good enantioselectivities by the title reaction of aldimines such as 1 with Danishefsky's diene 2.
Current Organic ChemistryReversal of Stereochemistry in Enantioselective Transformations. Can they be Planned or are they Just Accidental?
142 Citations2001Mukund P. Sibi, Mei Liu
Journal of the American Chemical SocietyAsymmetric Conjugate Addition of Thiols to a 3-(2-Alkenoyl)-2-oxazolidinone Catalyzed by the DBFOX/Ph Aqua Complex of Nickel(II) Perchlorate
142 Citations1999Shuji Kanemasa, Yoji Oderaotoshi +1 more
Journal of the American Chemical SocietyMechanism of Enantioselective Ti-Catalyzed Strecker Reaction: Peptide-Based Metal Complexes as Bifunctional Catalysts
131 Citations2001Nathan S. Josephsohn, Kevin W. Kuntz +2 more
Kinetic, structural, and stereochemical data regarding the mechanism of Ti-catalyzed addition of cyanide to imines in the presence of Schiff base peptide ligands illustrate that these non-C2-symmetric catalysts likely operate in a bifunctional fashion.
The Journal of Organic ChemistryAsymmetric Strecker Synthesis Using Enantiopure Sulfinimines and Diethylaluminum Cyanide: The Alcohol Effect
119 Citations1996Franklin A. Davis, Padma Portonovo +2 more
The Journal of Organic ChemistryA Switch of Enantiofacial Selectivities Using Designed Similar Chiral Ligands in Zirconium-Catalyzed Asymmetric Aza Diels−Alder Reactions
115 Citations1999Shū Kobayashi, Ken‐ichi Kusakabe +2 more
Journal of the American Chemical SocietyTi-Catalyzed Regio- and Enantioselective Synthesis of Unsaturated α-Amino Nitriles, Amides, and Acids. Catalyst Identification through Screening of Parallel Libraries
113 Citations2000James Porter, Wolfgang Wirschun +3 more
The Journal of Organic ChemistryMolecular Sieve Dependent Absolute Stereoselectivity in Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reactions
110 Citations1998Kurt V. Gothelf, Rita G. Hazell +1 more
The Journal of Organic ChemistryApplications of the Sulfinimine-Mediated Asymmetric Strecker Synthesis to the Synthesis of α-Alkyl α-Amino Acids
107 Citations2000Franklin A. Davis, Seung Woong Lee +2 more
Addition of Et(2)AlCN and i-PrOH to ketosulfinimines (N-sulfinyl imines) affords corresponding alpha-alkyl alpha-amino nitriles in moderate to good yields.
TetrahedronAsymmetric Diels-Alder reactions catalyzed by chiral lanthanide(III) trifluoromethanesulfonates. Unique structure of the triflate and stereoselective synthesis of both enantiomers using a single chiral source and a choice of achiral ligands
107 Citations1994Shū Kobayashi, Haruro Ishitani +2 more
Tetrahedron AsymmetrySc(BINOL)2Li: a new heterobimetallic catalyst for the asymmetric Strecker reaction
101 Citations2001Murielle Chavarot, Janice J. Byrne +2 more
Organic LettersAsymmetric Hydrocyanation of Hydrazones Catalyzed by Lanthanide−PYBOX Complexes
92 Citations2003John M. Keith, Eric N. Jacobsen
The asymmetric addition of HCN to hydrazones is catalyzed in high yield and good-to-excellent enantioselectivity by the easily prepared (PhPYBOX)ErCl3 complex, which constitutes the first example of asymmetric catalytic hydrocyanation of hydrazone.
SynlettEnantioselective Strecker Reaction Promoted by Chiral N-Oxides
84 Citations2001Bo Liu, Xiaoming Feng +4 more
Tetrahedron LettersEnantioselective Strecker-type reaction promoted by polymer-supported bifunctional catalyst
79 Citations2001Hiroyuki Nogami, Shigeki Matsunaga +2 more
Journal of the American Chemical SocietyHydrocyanation. IV. New hydrocyanation methods using hydrogen cyanide and an alkylaluminum, and an alkylaluminum cyanide
76 Citations1972Wataru Nagata, M. YOSHIOKA +1 more
Tetrahedron LettersAsymmetric Strecker reactions of ketimines catalysed by titanium-based complexes
74 Citations2000Janice J. Byrne, Murielle Chavarot +2 more
Tetrahedron LettersThe first enantioselective synthesis of both Diels-Alder enantiomers with the same bis(oxazoline)-magnesium perchlorate chiral catalyst
67 Citations1996Giovanni Desimoni, Giuseppe Faita +1 more
Tetrahedron LettersAsymmetric strecker synthesis using enantiopure sulfinimines: A convenient synthesis of α-amino acids
67 Citations1994Franklin A. Davis, Rajarathnam E. Reddy +1 more
Tetrahedron LettersTemperature-effected tuning of enantioselectivity in asymmetric catalysis
62 Citations1998Junzo Otera, Katsumasa Sakamoto +2 more
The Journal of Organic ChemistryHighly diastereoselective hydrocyanation of .beta.-keto sulfoxides: synthesis of enantiomerically pure cyanohydrin derivatives
58 Citations1992J.L.G. Ruano, Ana M. Martı́n Castro +1 more
Organic LettersMasked Oxo Sulfinimines (<i>N</i>-Sulfinyl Imines) in the Asymmetric Synthesis of Proline and Pipecolic Acid Derivatives
54 Citations2001Franklin A. Davis, Huiming Zhang +1 more
On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha-amino nitriles that afford oxo alpha-AMino acids on hydrolysis that are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield.
TetrahedronChiral Lewis acid controlled Diels-Alder reaction: Factors affecting the stereoselective formation of both enantiomers in the bis(oxazoline)-magnesium catalyzed process
54 Citations1998Paolo Carbone, Giovanni Desimoni +3 more
The Journal of Organic ChemistryConcise Asymmetric Synthesis of β-Hydroxy α-Amino Acids Using the Sulfinimine-Mediated Asymmetric Strecker Synthesis: Phenylserine and β-Hydroxyleucine
52 Citations2000Franklin A. Davis, Vaidyanathan Srirajan +2 more
Tetrahedron4-Naphthyl-substituted bis(oxazoline): A new, easily recoverable and efficient chiral ligand in asymmetric catalysis of the Diels-Alder reaction
48 Citations1998Stefano Crosignani, Giovanni Desimoni +2 more
The Journal of Organic ChemistrySynthetic uses of open-chain analogs of Reissert compounds
46 Citations1980William E. McEwen, Anthony V. Grossi +2 more
TetrahedronAn asymmetric conjugate addition reaction of lithium organocopper reagent controlled by a chiral amidophosphine
41 Citations1999Motomu Kanai, Yuichi Nakagawa +1 more
Tetrahedron LettersHydrogenation asymetrique a l'aide du complexe DIOXOP-Rh(I) voie dihydro ou voie insaturee.
41 Citations1981Denis Sinou
The Journal of Organic ChemistryAsymmetric Synthesis of Polyhydroxy α-Amino Acids with the Sulfinimine-Mediated Asymmetric Strecker Reaction: 2-Amino 2-Deoxy <scp>l</scp>-Xylono-1,5-lactone (Polyoxamic Acid Lactone)
40 Citations2002Franklin A. Davis, Kavirayani R. Prasad +1 more
Polyhydroxylated sulfinimines derived from protected 1,2-O-isopropyliden-L-threoses undergo the sulfininimine-mediated Strecker syntheses to give alpha-amino nitriles in good yield and de.
Organic LettersUnprecedented Effects of Achiral Oxazolidinones on Enantioselective Radical-Mediated Conjugate Additions Using a Chiral Zinc Triflate
39 Citations2000Masatoshi Murakata, Hideyuki Tsutsui +1 more
TetrahedronSynthesis of enantiomerically pure ethylenediamines from chiral sulfinimines: a new twist to the Strecker reaction
38 Citations2001Stéphane Mabic, Alex Cordi
European Journal of Organic ChemistryLewis Base-Catalyzed Addition of Trialkylaluminum Compounds to Epoxides
35 Citations2001Christoph Schneider, Jörg Brauner
ChiralityNovel chiral sulfur‐containing ferrocenyl ligands for palladium‐catalyzed asymmetric allylic substitution
34 Citations2003Shuichi Nakamura, Takeo Fukuzumi +1 more
New chiral ferrocenyl ligands having chiral sulfinyl and phosphinyl groups were prepared and the palladium-catalyzed allylic substitution reaction using these chiral ligands showed good enantioselectivity.
The Journal of Organic ChemistrySynthesis and Dienophilic Behavior of Enantiomerically Pure (<i>Z</i>)-3-<i>p</i>-Tolylsulfinylacrylonitriles
34 Citations1998J.L.G. Ruano, Antonio Esteban Gamboa +3 more
Tetrahedron AsymmetryStereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: a route to enantiopure β-amino-α-hydroxy acids
33 Citations2001José M. Andrés, M. Alejandra Martínez +2 more
Tetrahedron AsymmetryA practical stereoselective synthesis of (2R,3S)-alloisoleucine
32 Citations1999Padma Portonovo, Bo Liang +1 more
Tetrahedron LettersLewis base-catalyzed addition of triethylaluminum to epoxides
28 Citations2000Christoph Schneider, Jörg Brauner
Angewandte Chemie International EditionStereoselective Hydrocyanation of Alkenyl Sulfoxides as a Method to Highly Enantiomerically Enriched Compounds with Tertiary and Quaternary Chiral Carbon Atoms
26 Citations2001J.L.G. Ruano, Marta Cifuentes García +3 more
Terminal alkynes are easily transformed into enantiomerically enriched compounds containing tertiary and quaternary carbon atoms and can be undergo reaction to form the desired products.
Tetrahedron LettersStereoselective addition of cyanide reagents to nitrones
24 Citations1995F. L. MERCHAN, Pedro Merino +1 more
Trimethylsilyl cyanide was found to add to the nitrone 1 with essentially complete syn-stereoselectivity in excellent yields.
Organic LettersFirst Highly Stereoselective Synthesis of Fungicide Systhane
19 Citations2001J.L.G. Ruano, Marta Cifuentes García +2 more
The sulfinyl group controls the two key steps of the synthetic sequence, the highly stereoselective hydrocyanation of vinyl sulfoxides with Et(2)AlCN and the further introduction of the proper functionality into the molecule.
TetrahedronHighly diastereoselective Hydrocyanation of α-sulfinyl cycloalkanones
18 Citations1994Ana Escribano, J.L.G. Ruano +2 more
ChemInformChemInform Abstract: Ti‐Catalyzed Regio‐ and Enantioselective Synthesis of Unsaturated α‐Amino Nitriles, Amides and Acids. Catalyst Identification Through Screening of Parallel Libraries.
2 Citations2000James R. Porter, Wolfgang Wirschun +3 more
