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Asymmetric Synthesis of α‐Chiral Allylic Silanes by Enantioconvergent γ‐Selective Copper(I)‐Catalyzed Allylic Silylation
Author(s) -
Delvos Lukas B.,
Vyas Devendra J.,
Oestreich Martin
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201300648
Subject(s) - silanes , allylic rearrangement , silylation , copper , chemistry , organic chemistry , catalysis , silane
Gamma way : Regio‐ and enantioselective allylic substitution with a silicon nucleophile generated by copper(I)‐catalyzed SiB bond activation provides direct access to α‐chiral allylic silanes from linear acceptors. The enantioconvergent catalysis employing McQuade's six‐membered N‐heterocyclic‐carbene–copper(I) catalyst is applicable to aryl‐ and alkyl‐substituted allylic phosphates (see scheme).