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J Am Chem Soc. 2008 Jun 4;130(22):6910-1. doi: 10.1021/ja800829y. Epub 2008 May 8.

Asymmetric copper-catalyzed synthesis of alpha-amino boronate esters from N-tert-butanesulfinyl aldimines.

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1
Department of Chemistry, University of California, Berkeley, California 94720, USA.

Abstract

A general and efficient new method for the asymmetric synthesis of alpha-amino boronate esters has been developed. The key step is the Cu(I)-catalyzed addition of bis(pinacolato)diboron to N-tert-butanesulfinyl aldimines, which proceeds in good yields (52-88%) and with very high diastereoselectivities (>96:2) for a variety of aldimine substrates. This method was applied to an efficient synthesis of bortezomib, a potent alpha-amino boronic acid inhibitor of the proteasome that is in clinical use for the treatment of multiple myeloma and mantle cell lymphoma.

PMID:
18461938
DOI:
10.1021/ja800829y
[Indexed for MEDLINE]

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