Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 42, Pages 13501-13509Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200229
Keywords
allenes; chirality; cyclization; electrophilic addition; iodine
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Funding
- National Basic Research Program of China [2011CB808700]
- NSF of China [21232006, 21174039]
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A highly stereoselective iodolactonization of 4-allenoic acids with a new sterically demanding electrophilic iodination reagent to afford optically active ?-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-beta,?-disubstituted ?-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.
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