title: 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.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry, Institution RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Uxue
authors.initials: U
authors.lastname: Uria
authors.forename: Carlos
authors.initials: C
authors.lastname: Vila
authors.forename: Ming-Yuan
authors.initials: MY
authors.lastname: Lin
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D002839:Chromans; D014810:Vitamin E; D006046:Gold
keywords: allylic alkylation; chromans; gold catalysis; tocopherol; vitamin E