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Synthesis of enantiomerically pure β- and γ-amino acid derivatives using functionalized organozinc reagents

Lookup NU author(s): Professor Richard Jackson

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Abstract

β-Amido zinc reagents 4 and 5 readily undergo β-elimination when prepared in THF, but when a polar aprotic solvent such as DMF is employed, β-elimination is suppressed. Using DMF, reaction of 4 with aryl iodides provides β-homophenylalanine derivatives (12 examples, 20-89% yield), and analogous reactions of 5 give γ-bishomophenylalanine derivatives (7 examples, 34-80% yield). The related zinc/copper reagents 17 and 18 are also useful intermediates that undergo subsequent cross-coupling reactions with a wide range of electrophiles (9 examples, 28-87% yield).

Publication metadata

Author(s): Dexter CS, Jackson RFW, Elliott J

Publication type: Article

Publication status: Published

Journal: Journal of Organic Chemistry

Year: 1999

Volume: 64

Issue: 20

Pages: 7579-7585

Print publication date: 01/10/1999

ISSN (print): 0022-3263

ISSN (electronic): 1520-6904

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/jo990941y

DOI: 10.1021/jo990941y

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