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Modified Julia Olefination on Sugar‐Derived Lactones: Synthesis of Difluoro‐ exo ‐glycals
Author(s) -
Habib Samuel,
Gueyrard David
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403175
Subject(s) - chemistry , sugar , stereoselectivity , microwave irradiation , organic chemistry , glycal , sequence (biology) , stereochemistry , catalysis , biochemistry
We report the preparation of difluoro‐ exo ‐glycals by gem ‐difluoroolefination of benzylated sugar‐derived lactones using a modified Julia reaction. The addition is highly stereoselective, and the Smiles‐rearrangement–elimination sequence can be carried out under microwave irradiation.