Synlett 2009(10): 1651-1654  
DOI: 10.1055/s-0029-1217348
CLUSTER
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of trans-β-Lactams Using a Simple Multifunctional Catalyst

Ciby J. Abraham, Daniel H. Paull, Cajetan Dogo-Isonagie, Thomas Lectka*
Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA
Fax: +1(410)5168420; e-Mail: lectka@jhu.edu ;
Further Information

Publication History

Received 9 March 2009
Publication Date:
02 June 2009 (online)

Abstract

A catalytic, highly diastereoselective process for the synthesis of trans-β-lactams is reported. This system is based on a phosphonium fluoride precatalyst that both activates the nucleophile and directs the reaction process for high yield and diastereo­selectivity.

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1

Current address: Center for Biomedical Research, HIV and AIDS Program, Population Council, 1230 York Avenue, New York, NY 10065, USA.

2

Current address: National Institute of Diabetes and Digestive and Kidney Diseases, 9000 Rockville Pike Building 8 Rm. 1A-19, Bethesda, MD 20892, USA.

13

Use of the corresponding phosphonium phenoxide provided lower yields and a much slower reaction.

14

Control experiments whereby a cis- or mixed-lactam was mixed with the precatalyst or eventual catalyst or phenoxide showed no hint of epimerization.

15

We did see the analogous open, silylated product in the o-QM cyclization reaction, which subsequently cyclized upon fluoride treatment. See ref. 11 for more information.