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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
Author(s) -
Das Biswanath,
Venkateswarlu Katta,
Krishnaiah Maddeboina,
Holla Harish,
Majhi Anjoy
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690141
Subject(s) - chemistry , sulfonium , stereoselectivity , bromide , allyl bromide , adduct , medicinal chemistry , organic chemistry , catalysis , salt (chemistry)
Treatment of Baylis–Hillman adducts 1 with bromo(dimethyl)sulfonium bromide, Br(Me 2 )S + Br − , 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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