Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction
Journal of the American Chemical SocietyPublished 27 September 2010
Lindsay M. Repka, Jane Ni, Sarah E. Reisman
Citations216
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
P(R)-BINOL·SnCl(4) was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines, expected to facilitate the total synthesis of pyrroleindoline alkaloids.
Abstract
(R)-BINOL·SnCl(4) was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.
Keywords
ChemistryMedicineBiochemistry, Genetics and Molecular Biology
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