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Synlett 2006(19): 3346-3348  
DOI: 10.1055/s-2006-951550
LETTER
© Georg Thieme Verlag Stuttgart · New York

Aldol Reactions of α-Bromoalkyl Phenyl Ketones and Aldehydes with Tin(IV) Iodide and Tetrabutylammonium Iodide

Yoshiro Masuyama*, Masaru Ohtsuka, Ayako Kondo
Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan
Fax: +81(3)32383361; e-Mail: y-masuya@sophia.ac.jp;
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Publication History

Received 15 September 2006
Publication Date:
23 November 2006 (online)

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Abstract

Aldol reactions of α-bromoacetophenone and aldehydes in dichloromethane produced the corresponding E-α,β-unsaturated ketones at 25 °C with one equimolar amount of tin(IV) iodide, one equimolar amount of tetrabutylammonium iodide and one equimolar amount of N,N-diisopropylethylamine, and produced the corresponding β-hydroxy ketones at -80 °C with one equimolar amount of tin(IV) iodide and two equimolar amounts of tetrabutylammonium iodide. Using one equimolar amount of tin(IV) iodide and two equimolar amounts of tetrabutylammonium iodide at -80 °C in dichloromethane, α-bromopropiophenone reacted with aldehydes to afford the corresponding syn-α-methyl-β-hydroxy ketones selectively.

Key words

aldol reactions - diastereoselectivity - tin - enones - β-hydroxyketones

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