The importance of phosphine-to-rhodium ratios in enantioselective hydroborations

Kevin Burgess; Wilfred A. van der Donk

doi:10.1016/0020-1693(94)03860-0

The importance of phosphine-to-rhodium ratios in enantioselective hydroborations

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Abstract

Catalyzed hydroborations of several 1,1-disubstituted aryl alkenes were studied. Formation of tertiary alcohols (after oxidation) was favored when high phosphine-to-rhodium ratios were used. Enantioselective variants of this process can give chiral primary and tertiary alcohols with different enantioselectivities indicative of mechanistic differences. Measurements of product optical yields as a function of optical purities of the catalyst gave a linear correlation. The mechanistic implications of these data are discussed.

Original language	English (US)
Pages (from-to)	93-98
Number of pages	6
Journal	Inorganica Chimica Acta
Volume	220
Issue number	1-2
DOIs	https://doi.org/10.1016/0020-1693(94)03860-0
State	Published - Jun 1 1994
Externally published	Yes

Keywords

Catalysis
Enantioselectivity
Hydroboration
Phosphine complexes
Rhodium complexes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

Online availability

10.1016/0020-1693(94)03860-0

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title = "The importance of phosphine-to-rhodium ratios in enantioselective hydroborations",

abstract = "Catalyzed hydroborations of several 1,1-disubstituted aryl alkenes were studied. Formation of tertiary alcohols (after oxidation) was favored when high phosphine-to-rhodium ratios were used. Enantioselective variants of this process can give chiral primary and tertiary alcohols with different enantioselectivities indicative of mechanistic differences. Measurements of product optical yields as a function of optical purities of the catalyst gave a linear correlation. The mechanistic implications of these data are discussed.",

keywords = "Catalysis, Enantioselectivity, Hydroboration, Phosphine complexes, Rhodium complexes",

author = "Kevin Burgess and {van der Donk}, {Wilfred A.}",

note = "Funding Information: This work was supported by the National Science Foundationa nd the Robert A. Welch Foundation.K .B. thanks the National Institute of Health for a Career DevelopmentA ward, and the Alfred P. Sloan Foundation for a Scholarship.",

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doi = "10.1016/0020-1693(94)03860-0",

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T1 - The importance of phosphine-to-rhodium ratios in enantioselective hydroborations

AU - Burgess, Kevin

AU - van der Donk, Wilfred A.

N1 - Funding Information: This work was supported by the National Science Foundationa nd the Robert A. Welch Foundation.K .B. thanks the National Institute of Health for a Career DevelopmentA ward, and the Alfred P. Sloan Foundation for a Scholarship.

PY - 1994/6/1

Y1 - 1994/6/1

N2 - Catalyzed hydroborations of several 1,1-disubstituted aryl alkenes were studied. Formation of tertiary alcohols (after oxidation) was favored when high phosphine-to-rhodium ratios were used. Enantioselective variants of this process can give chiral primary and tertiary alcohols with different enantioselectivities indicative of mechanistic differences. Measurements of product optical yields as a function of optical purities of the catalyst gave a linear correlation. The mechanistic implications of these data are discussed.

AB - Catalyzed hydroborations of several 1,1-disubstituted aryl alkenes were studied. Formation of tertiary alcohols (after oxidation) was favored when high phosphine-to-rhodium ratios were used. Enantioselective variants of this process can give chiral primary and tertiary alcohols with different enantioselectivities indicative of mechanistic differences. Measurements of product optical yields as a function of optical purities of the catalyst gave a linear correlation. The mechanistic implications of these data are discussed.

KW - Catalysis

KW - Enantioselectivity

KW - Hydroboration

KW - Phosphine complexes

KW - Rhodium complexes

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The importance of phosphine-to-rhodium ratios in enantioselective hydroborations

Abstract

Keywords

ASJC Scopus subject areas

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