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
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2014-07-02Online Publication Date
2014-07-02Print Publication Date
2014-08Permanent link to this record
http://hdl.handle.net/10754/563681Metadata
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.Citation
Yang, 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/ol501424fSponsors
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 LettersPubMed ID
24987938Relations
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