Download PDF
Synthesis 2007(15): 2365-2369  
DOI: 10.1055/s-2007-983775
PAPER
© Georg Thieme Verlag Stuttgart · New York

Addition of Functionalized Nucleophiles to a Bridgehead Bromoketone

Michael Harmata*, Sumrit Wacharasindhu
Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA
Fax: +1(573)8822754; e-Mail: harmataM@missouri.edu;
Further Information

Publication History

Received 6 March 2007
Publication Date:
12 July 2007 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of bromoketone 1 with a variety of functionalized organolithiums is presented. In most cases, carbonyl addition followed by quasi-Favorskii rearrangement takes place to afford the rearrangement product in good yield. The utility of products from such a reaction is demonstrated in the synthesis of 22 from 14 via allylation and ring-opening/ring-closing metathesis.

Key words

cycloaddition - quasi-Favorskii rearrangement - lithium - metathesis