Copper‐Catalyzed Regio‐ and Enantioselective Addition of Silicon Grignard Reagents to Alkenes Activated by Azaaryl Groups | Zendy

Mao Wenbin | Zendy; Xue Weichao | Zendy; Irran Elisabeth | Zendy; Oestreich Martin | Zendy

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Copper‐Catalyzed Regio‐ and Enantioselective Addition of Silicon Grignard Reagents to Alkenes Activated by Azaaryl Groups

Author(s) -

Mao Wenbin,

Xue Weichao,

Irran Elisabeth,

Oestreich Martin

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.201905934

Subject(s) - enantioselective synthesis , catalysis , chemistry , reagent , nucleophile , silicon , combinatorial chemistry , conjugate , benzoxazole , organic chemistry , enantiomer , medicinal chemistry , mathematical analysis , mathematics

A new application of silicon Grignard reagents in C(sp 3 )−Si bond formation is reported. With the aid of BF 3 ⋅OEt 2 , these silicon nucleophiles add across alkenes activated by various azaaryl groups under copper catalysis. An enantioselective version employing benzoxazole‐activated alkenes as substrates and a CuI‐josiphos complex as catalyst has been developed, forming the C(sp3)−Si bond with good to high enantiomeric ratios (up to 97:3). The method expands the toolbox for “conjugate addition” type C(sp 3 )−Si bond formation.

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