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

Handle URI:
http://hdl.handle.net/10754/563681
Title:
Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations
Authors:
Yang, Limin; Wang, Fei; Lee, Richmond; Lv, Yunbo; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Zhong, Guofu
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; Chemical Science Program; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC); HCL
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
Issue Date:
Aug-2014
DOI:
10.1021/ol501424f
PubMed ID:
24987938
Type:
Article
ISSN:
15237060
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.
Is 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/ccyl49y; DOI:10.5517/ccyl49y; HANDLE:http://hdl.handle.net/10754/624714
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorYang, Liminen
dc.contributor.authorWang, Feien
dc.contributor.authorLee, Richmonden
dc.contributor.authorLv, Yunboen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorZhong, Guofuen
dc.date.accessioned2015-08-03T12:06:09Zen
dc.date.available2015-08-03T12:06:09Zen
dc.date.issued2014-08en
dc.identifier.issn15237060en
dc.identifier.pmid24987938en
dc.identifier.doi10.1021/ol501424fen
dc.identifier.urihttp://hdl.handle.net/10754/563681en
dc.description.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.en
dc.description.sponsorshipWe 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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleAsymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculationsen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentHCLen
dc.identifier.journalOrganic Lettersen
dc.contributor.institutionCollege of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, Chinaen
dc.contributor.institutionDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singaporeen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien
kaust.authorYang, Liminen
dc.relation.isSupplementedByYang, 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/ccyl49yen
dc.relation.isSupplementedByDOI:10.5517/ccyl49yen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624714en
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