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Unexpected Ring Expansion of the (3a S ,6a R )‐ γ ‐Thiolactone Moiety during the Introduction of the (+)‐Biotin Side Chain
Author(s) -
Huang Jian,
Xiong Fei,
Wang ZhongHua,
Chen FenEr
Publication year - 2009
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.200800435
Subject(s) - thiolactone , chemistry , moiety , ring (chemistry) , ketone , side chain , bromide , yield (engineering) , stereochemistry , organic chemistry , materials science , metallurgy , polymer
The reaction of vinylmagnesium bromide with the (3a S ,6a R )‐ γ ‐thiolactone 2 in THF afforded, after unexpected ring expansion of the γ ‐thiolactone moiety, the seven‐membered‐ring ketone 5 in excellent yield, instead of the expected tertiary alcohol 3 .