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

Authors

Joseph M. Dennis
Catherine M. Calyore
Jessica S. Sjoholm
Patrick J. Lutz
Joseph J. Gair
Jeffrey B. Johnson, Hope CollegeFollow

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

Recommended Citation

Dennis, Joseph M., Catherine M. Calyore, Jessica S. Sjoholm, Patrick J. Lutz, Joseph J. Gair and Jeffrey B. Johnson. "Nickel-Catalyzed Direct Addition of Diorganozinc Reagents to Phthalimides: Selective Formation of Gamma-Hydroxylactams." Synlett 24, no. 19 (2013): 2567-2570.