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

Type
Article
Authors
Yang, Limin
Wang, Fei
Lee, Richmond
Lv, Yunbo
Huang, Kuo-Wei cc
Zhong, Guofu
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2014-07-02
Online Publication Date
2014-07-02
Print Publication Date
2014-08
Permanent link to this record
http://hdl.handle.net/10754/563681

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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.
Sponsors
We thank the NSFC (21302032 and 21373073) and the PCSIRT (IRT 1231) for financial support. G.Z. appreciates a QjanJiang Scholar from Zhejiang Province in China.
Publisher
American Chemical Society (ACS)
Journal
Organic Letters
DOI
10.1021/ol501424f
PubMed ID
24987938
Relations
Is Supplemented By:
  • [Dataset]
    Yang, L., Wang, F., Lee, R., Lv, Y., Huang, K.-W., & Zhong, G. (2014). CCDC 881370: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccyl49y. DOI: 10.5517/ccyl49y HANDLE: 10754/624714
Collections
Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)