Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes

Rama K. Bhatt; Jianhua Ye; J. R. Falck

doi:10.1016/S0040-4039(00)73117-0

Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes

Rama K. Bhatt, Jianhua Ye, J. R. Falck

Biochemistry

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

14 Scopus citations

Abstract

Aldehydes, but not ketones, are converted to α-hydroxystannanes via the corresponding silyl ethers in good to excellent yields by Bu₄NCN catalyzed addition of Bu₃SnSiMe₃ and hydrolytic isolation. Modest asymmetric induction was observed using a chiral quaternary ammonium cyanide catalyst.

Original language	English (US)
Pages (from-to)	4081-4084
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(00)73117-0
State	Published - Jun 13 1994

Keywords

chiral induction
stannylhydrin
tin
trimethyl(tributylstannyl)silane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)73117-0

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title = "Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes",

abstract = "Aldehydes, but not ketones, are converted to α-hydroxystannanes via the corresponding silyl ethers in good to excellent yields by Bu4NCN catalyzed addition of Bu3SnSiMe3 and hydrolytic isolation. Modest asymmetric induction was observed using a chiral quaternary ammonium cyanide catalyst.",

keywords = "chiral induction, stannylhydrin, tin, trimethyl(tributylstannyl)silane",

author = "Bhatt, {Rama K.} and Jianhua Ye and Falck, {J. R.}",

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T1 - Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes

AU - Bhatt, Rama K.

AU - Ye, Jianhua

AU - Falck, J. R.

PY - 1994/6/13

Y1 - 1994/6/13

N2 - Aldehydes, but not ketones, are converted to α-hydroxystannanes via the corresponding silyl ethers in good to excellent yields by Bu4NCN catalyzed addition of Bu3SnSiMe3 and hydrolytic isolation. Modest asymmetric induction was observed using a chiral quaternary ammonium cyanide catalyst.

AB - Aldehydes, but not ketones, are converted to α-hydroxystannanes via the corresponding silyl ethers in good to excellent yields by Bu4NCN catalyzed addition of Bu3SnSiMe3 and hydrolytic isolation. Modest asymmetric induction was observed using a chiral quaternary ammonium cyanide catalyst.

KW - chiral induction

KW - stannylhydrin

KW - tin

KW - trimethyl(tributylstannyl)silane

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U2 - 10.1016/S0040-4039(00)73117-0

DO - 10.1016/S0040-4039(00)73117-0

M3 - Article

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VL - 35

SP - 4081

EP - 4084

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Convenient preparation of α-trimethylsilyloxy- and α-hydroxystannanes from aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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