Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

Limin Yang, Fei Wang, Richmond Lee, Yunbo Lv, Kuo-Wei Huang, Guofu Zhong

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

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. © 2014 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)3872-3875
Number of pages4
JournalOrganic Letters
Volume16
Issue number15
DOIs
StatePublished - Jul 2 2014

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations'. Together they form a unique fingerprint.

Cite this