期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 354, 期 9, 页码 1617-1639出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200031
关键词
acylation; asymmetric reactions; homoenolates; N-heterocyclic carbenes; organocatalysis
资金
- NIGMS [GM72586]
- Lilly
- National Science Foundation [0822211]
- Division Of Graduate Education
- Direct For Education and Human Resources [0822211] Funding Source: National Science Foundation
N-heterocyclic carbenes (NHC) are well known for their role in catalyzing benzoin and Stetter reactions: the generation of acyl anion equivalents from simple aldehydes to react with a variety of electrophiles. However, when an aldehyde bearing a leaving group or unsaturation adjacent to the acyl anion equivalent is subjected to an NHC, a new avenue of reactivity is unlocked, leading to a number of novel transformations which can generate highly complex products from simple starting materials, many of which are assembled through unconventional bond disconnections. The field of these new reactions those utilizing a-reducible aldehydes to access previously unexplored catalytic intermediates has expanded rapidly in the past eight years. This review aims to provide the reader with a historical perspective on the underlying discoveries that led to the current state of the art, a mechanistic description of these reactions, and a summary of the recent advances in this area.
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