Universität zu Köln

Pitchumani, Venkatachalam, Breugst, Martin and Lupton, David W. (2021). Enantioselective Rauhut-Currier Reaction with beta-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes. Org. Lett., 23 (24). S. 9413 - 9419. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

Full text not available from this repository.

Abstract

beta-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut-Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Pitchumani, Venkatachalam UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Lupton, David W. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-571060
DOI:	10.1021/acs.orglett.1c03554
Journal or Publication Title:	Org. Lett.
Volume:	23
Number:	24
Page Range:	S. 9413 - 9419
Date:	2021
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1523-7052
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language BAYLIS-HILLMAN REACTION; NUCLEOPHILICITY; HYDROACYLATION; CONSTRUCTION; UMPOLUNG; AMIDES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/57106