<i>N</i>-Heterocyclic Carbene Catalyzed [4 + 2] Annulation Reactions with in Situ Generated Heterocyclic <i>ortho</i>-Quinodimethanes
Organic LettersPublished 8 July 2016
Jianfeng Xu, Shiru Yuan, Maozhong Miao
Citations100
SJR quartileQ1
SJR score1.24
SNIP1.03
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TL;DR
The main features of this reaction include challenging direct C(sp(3))-H bond functionalizations, excellent enantioselectivities, readily available starting materials, mild reaction conditions, high efficiency, and operational simplicity.
Abstract
An efficient strategy for the in situ generation of heterocyclic ortho-quinodimethanes (oQDMs) from 2-methyl-heteroarene-3-carboxylic esters by N-heterocyclic carbene (NHC) catalysis is disclosed. These heterocyclic oQDMs undergo highly enantioselective [4 + 2] annulation reactions with isatin-derived ketimines to afford optically pure heteroarene-fused δ-lactams bearing a quaternary stereogenic center. The main features of this reaction include challenging direct C(sp(3))-H bond functionalizations, excellent enantioselectivities, readily available starting materials, mild reaction conditions, high efficiency, and operational simplicity.
Keywords
Chemistry
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