Journal
CHEMICAL SCIENCE
Volume 6, Issue 12, Pages 6986-6990Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc02485d
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Funding
- National Natural Science Foundation of China [21372239, 21202187]
- Scientific Research Foundation of Northwest AF University [Z111021501]
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By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo iodo-cycloetherification/Wagner-Meerwein rearrangement of allyl alcohols en route to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner-Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration.
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