Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes

Anyu He; J R Falck

doi:10.1002/anie.200802313

Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes

Anyu He, J R Falck

Biochemistry

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

22 Scopus citations

Abstract

(Chemical Equation Presented) Li and Mg are pesky: A catalytic asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes (1) in good to excellent yields and enantioselectivities was achieved (see scheme; PG=protecting group; L*=chiral ligand). Compound 1 was isolated as an ester or thiocarbamate, and the reagent was prepared from equimolar amounts of nBu₃SnH and Et₂Zn in dimethoxyethane. Conditions employing lithium or magnesium ions suppress enantioselectivity.

Original language	English (US)
Pages (from-to)	6586-6589
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	35
DOIs	https://doi.org/10.1002/anie.200802313
State	Published - Aug 18 2008

Keywords

Aldehydes
Asymmetric synthesis
Organometallic compounds
Tin
Zinc

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200802313

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abstract = "(Chemical Equation Presented) Li and Mg are pesky: A catalytic asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes (1) in good to excellent yields and enantioselectivities was achieved (see scheme; PG=protecting group; L*=chiral ligand). Compound 1 was isolated as an ester or thiocarbamate, and the reagent was prepared from equimolar amounts of nBu3SnH and Et2Zn in dimethoxyethane. Conditions employing lithium or magnesium ions suppress enantioselectivity.",

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author = "Anyu He and Falck, {J R}",

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AU - He, Anyu

AU - Falck, J R

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N2 - (Chemical Equation Presented) Li and Mg are pesky: A catalytic asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes (1) in good to excellent yields and enantioselectivities was achieved (see scheme; PG=protecting group; L*=chiral ligand). Compound 1 was isolated as an ester or thiocarbamate, and the reagent was prepared from equimolar amounts of nBu3SnH and Et2Zn in dimethoxyethane. Conditions employing lithium or magnesium ions suppress enantioselectivity.

AB - (Chemical Equation Presented) Li and Mg are pesky: A catalytic asymmetric synthesis of α-(hydroxyalkyl)-tri-n-butylstannanes (1) in good to excellent yields and enantioselectivities was achieved (see scheme; PG=protecting group; L*=chiral ligand). Compound 1 was isolated as an ester or thiocarbamate, and the reagent was prepared from equimolar amounts of nBu3SnH and Et2Zn in dimethoxyethane. Conditions employing lithium or magnesium ions suppress enantioselectivity.

KW - Aldehydes

KW - Asymmetric synthesis

KW - Organometallic compounds

KW - Tin

KW - Zinc

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JF - Angewandte Chemie - International Edition

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ER -

Synthesis of enantioenriched α-(hydroxyalkyl)-tri-n-butylstannanes

Abstract

Keywords

ASJC Scopus subject areas

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