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A Rapid and Efficient Stereoselective Synthesis of (Z)- and (E)-Allyl Bromides from Baylis–Hillman Adducts Using Bromo(dimethyl)sulfonium Bromide

✍ Scribed by Biswanath Das; Katta Venkateswarlu; Maddeboina Krishnaiah; Harish Holla; Anjoy Majhi

Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 78 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690141

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✦ Synopsis

Treatment of Baylis-Hillman adducts 1 with bromo(dimethyl)sulfonium bromide, Br(Me 2 )S + Br À , in MeCN was found to stereoselectively afford (Z)-and (E)-allyl bromides 2. The reaction is rapid at room temperature, high-yielding, and highly stereoselective.

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