ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated Butyrolactams: Michael Addition to alpha,beta-Unsaturated Aldehydes and Ketones

Roy, Soumya Jyoti Singha and Mukherjee, Santanu (2018) Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated Butyrolactams: Michael Addition to alpha,beta-Unsaturated Aldehydes and Ketones. In: JOURNAL OF ORGANIC CHEMISTRY, 83 (19). pp. 12071-12085.

[img] PDF
Jou_Org_Che_83-19_12071_2018.pdf - Published Version
Restricted to Registered users only

Download (2MB) | Request a copy
Official URL: http://dx.doi.org/10.1021/acs.joc.8b02051

Abstract

Nucleophilic reactivity of deconjugated butyrolactams has been demonstrated for enantioselective Michael additions to alpha,beta-unsaturated aldehydes and ketones. These reactions are catalyzed by diphenylprolinol silyl ether and trans-1,2-diaminocyclohexane-derived bifunctional primary aminothiourea, respectively, producing the Michael adducts with moderate diastereoselectivities and good to excellent enantioselectivities (up to 99:1 er). Unlike in the case of structurally related deconjugated butenolides where vinylogous addition is prevalent, an exclusive alpha-addition is observed for deconjugated butyrolactams.

Item Type: Journal Article
Additional Information: Copy right for this article belong to AMER CHEMICAL SOC
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 29 Oct 2018 15:31
Last Modified: 29 Oct 2018 15:31
URI: http://eprints.iisc.ac.in/id/eprint/60990

Actions (login required)

View Item View Item