Nickel-Catalyzed Direct Addition of Diorganozinc Reagents to Phthalimides: Selective Formation of Gamma-Hydroxylactams

Document Type

Article

Publication Date

12-2-2013

Publication Source

Synlett

Volume Number

24

Issue Number

19

First Page

2567

Last Page

2570

Publisher

Georg Thieme Verlag

ISSN

0936-5214

Abstract

The nickel-catalyzed addition of diorganozinc reagents to phthalimides proceeds with excellent selectivity to provide 3-substituted-3-hydroxyisoindolin-1-one products. These 3-hydroxy--lactams are produced cleanly in high yield with numerous examples of imide substitution and a broad range of diorganozinc reagents that are prepared and utilized without purification.

Keywords

Imide, Catalysis, Lactams, Organometallic Reagents, Nickel, Radical Cyclization, Chilenine

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