Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives | Zendy

Akiyama Sota | Zendy; Kubota Koji | Zendy; Mikus Malte S. | Zendy; Paioti Paulo H. S. | Zendy; Romiti Filippo | Zendy; Liu Qinghe | Zendy; Zhou Yuebiao | Zendy; Hoveyda Amir H. | Zendy; Ito Hajime | Zendy

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Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives

Author(s) -

Akiyama Sota,

Kubota Koji,

Mikus Malte S.,

Paioti Paulo H. S.,

Romiti Filippo,

Liu Qinghe,

Zhou Yuebiao,

Hoveyda Amir H.,

Ito Hajime

Publication year - 2019

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.201906283

Subject(s) - stereocenter , enantioselective synthesis , allylic rearrangement , aldimine , yield (engineering) , chemistry , catalysis , enantiomer , fluoride , organic chemistry , stereochemistry , materials science , metallurgy , inorganic chemistry

The first catalytic method for diastereo‐ and enantioselective synthesis of allylic boronates bearing a Z ‐trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with either a Z ‐ or E ‐allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z / E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.

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