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
Physical Sciences and Engineering (PSE) Division
KAUST Catalysis Center (KCC)
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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.
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)
Is Supplemented ByYang, 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
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