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2014•Organic LettersRequires access

Directed Metalation of 1-Ester-Substituted Indolizines: Base/Electrophile-Controlled Regioselective Functionalization

M. Amaral, Amanda A. Baumgartner, Ricardo Vessecchi, Giuliano C. Clososki

Open publisher page 59 citations

Abstract

A variety of C-2 and C-5 difunctionalized indolizines have been prepared through the reaction of 1-ester-substituted indolizines with organometallic bases followed by a reaction with different electrophiles. Metalation takes place under mild conditions allowing the isolation of a number of difunctionalized indolizines in good yields. The regioselectivity of the reaction appears to be governed by the nature of the base and electrophile.

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What this paper is about

A variety of C-2 and C-5 difunctionalized indolizines have been prepared through the reaction of 1-ester-substituted indolizines with organometallic bases followed by a reaction with different electrophiles. Metalation takes place under mild conditions allowing the isolation of a number of difunctionalized indolizines in good yields. The regioselectivity of the reaction appears to be governed by the nature of the base and electrophile.

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Available abstract

A variety of C-2 and C-5 difunctionalized indolizines have been prepared through the reaction of 1-ester-substituted indolizines with organometallic bases followed by a reaction with different electrophiles. Metalation takes place under mild conditions allowing the isolation of a number of difunctionalized indolizines in good yields. The regioselectivity of the reaction appears to be governed by the nature of the base and electrophile.

Key concepts: Electrophile, Regioselectivity, Metalation, Chemistry, Surface modification, Combinatorial chemistry, Base (topology), Organic chemistry

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