Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2014-07-02
Print Publication Date2014-08
Permanent link to this recordhttp://hdl.handle.net/10754/563681
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AbstractA 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.
CitationYang, L., Wang, F., Lee, R., Lv, Y., Huang, K.-W., & Zhong, G. (2014). Asymmetric NHC-Catalyzed Aza-Diels–Alder Reactions: Highly Enantioselective Route to α-Amino Acid Derivatives and DFT Calculations. Organic Letters, 16(15), 3872–3875. doi:10.1021/ol501424f
SponsorsWe 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.
PublisherAmerican Chemical Society (ACS)
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