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Asymmetric NHC-Catalyzed Aza-Diels-Alder Reactions: Highly Enantioselective Route to alpha-Amino Acid Derivatives and DFT Calculations
Journal article   Peer reviewed

Asymmetric NHC-Catalyzed Aza-Diels-Alder Reactions: Highly Enantioselective Route to alpha-Amino Acid Derivatives and DFT Calculations

Limin Yang, Fei Wang, Richmond Lee, Yunbo Lv, Kuo-Wei Huang and Guofu Zhong
Organic letters, Vol.16(15), pp.3872-3875
01/08/2014
DOI: https://doi.org/10.1021/ol501424f
PMID: 24987938

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with alpha-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations.

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