Download PDF
Synthesis 2006(10): 1572-1574  
DOI: 10.1055/s-2006-926465
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

In situ Generation and Nucleophilic Capture of 1,n-Dial Equivalents from 1,n-Dioates (α,ω-Diesters)

Thomas R. Hoye*, Lucas C. Kopel, Troy D. Ryba
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA
Fax: +1(612)6267541; e-Mail: hoye@chem.umn.edu;
Further Information

Publication History

Received 15 November 2005
Publication Date:
27 April 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.

Key words

nucleophilic additions - hydrides - reductions - tandem reactions - Wittig reactions