Synthesis 2005(15): 2609-2614  
DOI: 10.1055/s-2005-872144
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

3-Bromopropenyl Methyl Carbonate: A New Reagent for the α-Hydroxy Allylation Reaction of Aldehydes in Water

Marco Lombardo*, Filippo Pasi, Caterina Tiberi, Claudio Trombini*
Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: marco.lombardo@unibo.it ; e-Mail: claudio.trombini@unibo.it;
Further Information

Publication History

Received 13 June 2005
Publication Date:
04 August 2005 (eFirst)

Abstract

3-Bromopropenyl methyl carbonate reacts smoothly with aldehydes in the presence of zinc in a mixture of saturated aqueous NH4Cl and THF (9:1). Monoprotected alk-1-en-3,4-diols are formed in high yields and in short reaction times. The reaction is diastereoselective, saturated aldehydes afford anti-adducts, while α,β-unsaturated and aromatic aldehydes preferentially give the syn-isomers. Very simple conditions for the conversion of intermediate monocarbonate derivatives of alk-1-en-3,4-diols to cyclic carbonates are also reported.

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