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Catalytic Enantioselective Preparation of α‐Substituted Allylboronates: One‐Pot Addition to Functionalized Aldehydes and a Route to Chiral Allylic Trifluoroborate Reagents
Author(s) -
Carosi Lisa,
Hall Dennis G.
Publication year - 2007
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.200700975
Subject(s) - enantioselective synthesis , reagent , allylic rearrangement , tsuji–trost reaction , chemistry , catalysis , combinatorial chemistry , alkylation , organic chemistry
Well B‐haved! Boronyl groups are fully compatible in the copper‐catalyzed asymmetric alkylation with chiral phosphoramidites to afford acyclic α‐substituted allylic boronate reagents (see scheme, CuTC=copper(I) thiophene‐2‐carboxylate). This represents the first highly enantioselective catalytic approach to these boronate compounds, which are useful reagents in synthesis.