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.

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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
Publication:	JOURNAL OF ORGANIC CHEMISTRY
Publisher:	AMER CHEMICAL SOC
Additional Information:	Copy right for this article belong to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	29 Oct 2018 15:31
Last Modified:	29 Oct 2018 15:31
URI:	http://eprints.iisc.ac.in/id/eprint/60990

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