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Gold‐Catalyzed Asymmetric Allylic Substitution of Free Alcohols: An Enantioselective Approach to Chiral Chromans with Quaternary Stereocenters for the Synthesis of Vitamin E and Analogues
Author(s) -
Uria Uxue,
Vila Carlos,
Lin MingYuan,
Rueping Magnus
Publication year - 2014
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.201403768
Subject(s) - enantioselective synthesis , stereocenter , tsuji–trost reaction , allylic rearrangement , chemistry , metathesis , olefin fiber , stereochemistry , catalysis , alkylation , combinatorial chemistry , organic chemistry , polymerization , polymer
The enantioselective synthesis of α‐ and γ‐tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing a new enantioselective gold catalyzed intramolecular allylic alkylation reaction followed by an olefin cross‐metathesis as key steps. The methodology proved to be applicable to different olefins highlighting its potential for the synthesis of diverse libraries.