Stereoselective Mannich Reaction of α-Acetoxy-β-keto Esters with Isatin Imine: An Efficient Access to Vicinal Tetra-Substituted Stereocenters

Kaur J.; Preet Kaur B.; Islam N.; Chauhan P.; Singh Chimni S.

Full metadata record

DC Field	Value	Language
dc.rights.license	All Open Access, Bronze	-
dc.contributor.author	Kaur J.	en_US
dc.contributor.author	Preet Kaur B.	en_US
dc.contributor.author	Islam N.	en_US
dc.contributor.author	Chauhan P.	en_US
dc.contributor.author	Singh Chimni S.	en_US
dc.date.accessioned	2023-11-30T08:42:12Z	-
dc.date.available	2023-11-30T08:42:12Z	-
dc.date.issued	2021	-
dc.identifier.issn	1434193X	-
dc.identifier.other	EID(2-s2.0-85117125043)	-
dc.identifier.uri	https://dx.doi.org/10.1002/ejoc.202101047	-
dc.identifier.uri	http://localhost:8080/xmlui/handle/123456789/575	-
dc.description.abstract	A highly diastereo- and enantioselective Mannich reaction of α-acetoxy-β-keto esters with isatin imine was developed. The quinine thiourea organocatalyst smoothly promoted the asymmetric Mannich reaction to furnish various 3-substituted-3-aminooxindole derivatives bearing two adjacent tetra-substituted stereocenters in up to 93 % yield, up to 98 % ee with >20 : 1 dr. The transition state structure and absolute configuration of the obtained product were predicted using DFT calculations, and results from single crystal X-ray analysis are in agreement with the DFT studies. © 2021 Wiley-VCH GmbH	en_US
dc.language.iso	en	en_US
dc.publisher	John Wiley and Sons Inc	en_US
dc.source	European Journal of Organic Chemistry	en_US
dc.subject	Asymmetric synthesis	en_US
dc.subject	Isatin imine	en_US
dc.subject	Mannich reaction	en_US
dc.subject	Organocatalysis	en_US
dc.subject	α-Acetoxy-β-keto esters	en_US
dc.title	Stereoselective Mannich Reaction of α-Acetoxy-β-keto Esters with Isatin Imine: An Efficient Access to Vicinal Tetra-Substituted Stereocenters	en_US
dc.type	Journal Article	en_US
Appears in Collections:	Journal Article