Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Suman Chakrabarty; James M. Takacs

doi:10.1021/jacs.7b02324

Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Suman Chakrabarty, James M. Takacs

Chemistry

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

Original language	English (US)
Pages (from-to)	6066-6069
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	17
DOIs	https://doi.org/10.1021/jacs.7b02324
State	Published - May 3 2017

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes",

abstract = "Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.",

author = "Suman Chakrabarty and Takacs, {James M.}",

note = "Funding Information: Funding from the NIH National Institutes of General Medical Sciences (R01-GM100101) is gratefully acknowledged. We sincerely thank P. H. Dussault (UNL) for use of equipment and V. M. Shoba (UNL) for helpful discussions. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Chakrabarty, Suman

AU - Takacs, James M.

N1 - Funding Information: Funding from the NIH National Institutes of General Medical Sciences (R01-GM100101) is gratefully acknowledged. We sincerely thank P. H. Dussault (UNL) for use of equipment and V. M. Shoba (UNL) for helpful discussions. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/5/3

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N2 - Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

AB - Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.

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Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Abstract

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