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Synthesis 2011(23): 3815-3820
DOI: 10.1055/s-0031-1289304
DOI: 10.1055/s-0031-1289304
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkBoron Trihalide Mediated Haloallylation of Aryl Aldehydes and Its Application to the Preparation of (E)-1,3-Dienes
Further Information
Received
17 August 2011
Publication Date:
20 October 2011 (online)
Publication History
Publication Date:
20 October 2011 (online)
Abstract
In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene, provides a straightforward route to synthetically useful (E)-1,3-dienes. The mild reaction conditions, readily available starting materials, and high stereoselectivity make this two-step (E)-1,3-diene synthesis quite attractive.
Key words
boron trihalide - allylmetal - haloallylation - diene - stereoselectivity
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