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Synlett 2012(3): 468-472  
DOI: 10.1055/s-0031-1290313
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Vinylogous Aldol Reaction Triggered by Tetrabutylammonium Fluoride: A Highly Regioselective and Diastereoselective Addition of Cyclic β-Haloenals to Aromatic Aldehydes

Jingli Zhang, Lianghu Gu, Yuefa Gong*
School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China
Fax: +86(27)87543632; e-Mail: gongyf@mail.hust.edu.cn;
Further Information

Publication History

Received 1 November 2011
Publication Date:
19 January 2012 (online)

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Abstract

A new type of direct vinylogous aldol addition between cyclic β-haloenals and aromatic aldehydes promoted by TBAF has been developed. The reaction was carried out under mild conditions to provide highly functionalized δ-hydroxy-β-halo-α,β-unsaturated aldehydes with high diastereomeric ratios and low to good yields.

Key words

direct vinylogous aldol reaction - TBAF - cyclic β-haloenals - regio- and diastereoselectivity - homoallylic alcohols

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CCDC 825960 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.