Catalytic Enantioselective Preparation of α‐Substituted Allylboronates: One‐Pot Addition to Functionalized Aldehydes and a Route to Chiral Allylic Trifluoroborate Reagents | Zendy

Carosi Lisa | Zendy; Hall Dennis G. | Zendy

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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.

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