Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations
Type
Article
KAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Physical Sciences and Engineering (PSE) Division
KAUST Catalysis Center (KCC)
HCL
Date
2014-08Metadata
Show full item recordAbstract
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 LettersISSN
15237060PubMed ID
24987938Handle URI
http://hdl.handle.net/10754/563681Is Supplemented By
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/ccyl49yDOI:10.5517/ccyl49y
HANDLE:http://hdl.handle.net/10754/624714