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Stereoselective Iodolactonization of 4‐Allenoic Acids with Efficient Chirality Transfer: Development of a New Electrophilic Iodination Reagent
Author(s) -
Zhang Xiaobing,
Fu Chunling,
Yu Yihua,
Ma Shengming
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200229
Subject(s) - chemistry , electrophile , halogenation , diastereomer , chirality (physics) , stereoselectivity , enantiomer , reagent , steric effects , selectivity , lactone , organic chemistry , stereochemistry , catalysis , chiral symmetry , nambu–jona lasinio model , quark , physics , quantum mechanics
A highly stereoselective iodolactonization of 4‐allenoic acids with a new sterically demanding electrophilic iodination reagent to afford optically active γ‐butyrolactones has been developed. The reaction shows high efficiency of axial chirality transfer and excellent Z / E selectivity and has been applied to the synthesis of chiral cis ‐β,γ‐disubstituted γ‐butyrolactones to give very high diastereomeric and enantiomeric excess values. The reaction has been successfully utilized in the synthesis of naturally occurring compounds (+)‐ cis ‐whisky lactone and (+) ‐cis ‐3‐methyl‐4‐decanolide.