Rhodium(I)-Catalyzed Highly Enantioselective Insertion of Carbenoid into Si–H: Efficient Access to Functional Chiral Silanes | Zendy

Chen Diao | Zendy; DongXing Zhu | Zendy; MingHua Xu | Zendy

Open Access

Rhodium(I)-Catalyzed Highly Enantioselective Insertion of Carbenoid into Si–H: Efficient Access to Functional Chiral Silanes

Author(s) -

Chen Diao,

DongXing Zhu,

MingHua Xu

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b12960

Subject(s) - chemistry , enantioselective synthesis , rhodium , carbenoid , silanes , carbene , catalysis , insertion reaction , migratory insertion , kinetic isotope effect , medicinal chemistry , combinatorial chemistry , stereochemistry , deuterium , organic chemistry , physics , silane , quantum mechanics

The first rhodium(I)-catalyzed enantioselective Si-H insertion reaction of α-diazoesters and α-diazophosphonates has been developed. The use of a C1-symmetric chiral diene ligand enabled the asymmetric reaction to proceed under exceptionally mild conditions and give versatile chiral α-silyl esters and phosphonates with excellent enantioselectivities (up to 99% ee). The mechanism and stereochemical pathway of this novel Rh(I)-carbene-directed Si-H insertion was investigated by deuterium kinetic isotope effect experiments and DFT calculations.

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