Asymmetric NHC-catalyzed aza-diels–alder reactions: highly enantioselective route to α-amino acid derivatives and DFT calculations

L. Yang, F. Wang, R. Lee, Y. Lv, K.-W. Huang, and G. Zhong
Org Lett., 16(15), 3872-5, (2014)

Asymmetric NHC-catalyzed aza-diels–alder reactions: highly enantioselective route to α-amino acid derivatives and DFT calculations

Keywords

-amino acid derivatives, N-heterocyclic carbene

Abstract

​A facile N-heterocyclic carbene catalytic enantioselective aza-Diels–Alder reaction of oxodiazenes with α-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.

Code

DOI: 10.1021/ol501424f

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