Stereoselective photocycloaddition of silyl enol ethers to aldehydes. Configurational control of three stereogenic centers in oxetanes

Thorsten Bach

doi:10.1016/S0040-4039(00)78199-8

Stereoselective photocycloaddition of silyl enol ethers to aldehydes. Configurational control of three stereogenic centers in oxetanes

Thorsten Bach

University of Münster

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

25 Scopus citations

Abstract

The photocycloaddition of unsymmetrically substituted alkenes to an aldehyde leads to eight possible isomeric oxetanes. In sharp contrast to most other substrates, silyl enol ethers 1 which bear a vinylic β-substituent favor only a single stereo- and regioisomer 2 as major product of this reaction.

Original language	English
Pages (from-to)	5845-5848
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)78199-8
State	Published - 8 Aug 1994
Externally published	Yes

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10.1016/S0040-4039(00)78199-8

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title = "Stereoselective photocycloaddition of silyl enol ethers to aldehydes. Configurational control of three stereogenic centers in oxetanes",

abstract = "The photocycloaddition of unsymmetrically substituted alkenes to an aldehyde leads to eight possible isomeric oxetanes. In sharp contrast to most other substrates, silyl enol ethers 1 which bear a vinylic β-substituent favor only a single stereo- and regioisomer 2 as major product of this reaction.",

author = "Thorsten Bach",

year = "1994",

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doi = "10.1016/S0040-4039(00)78199-8",

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T1 - Stereoselective photocycloaddition of silyl enol ethers to aldehydes. Configurational control of three stereogenic centers in oxetanes

AU - Bach, Thorsten

PY - 1994/8/8

Y1 - 1994/8/8

N2 - The photocycloaddition of unsymmetrically substituted alkenes to an aldehyde leads to eight possible isomeric oxetanes. In sharp contrast to most other substrates, silyl enol ethers 1 which bear a vinylic β-substituent favor only a single stereo- and regioisomer 2 as major product of this reaction.

AB - The photocycloaddition of unsymmetrically substituted alkenes to an aldehyde leads to eight possible isomeric oxetanes. In sharp contrast to most other substrates, silyl enol ethers 1 which bear a vinylic β-substituent favor only a single stereo- and regioisomer 2 as major product of this reaction.

UR - https://www.scopus.com/pages/publications/0027978622

U2 - 10.1016/S0040-4039(00)78199-8

DO - 10.1016/S0040-4039(00)78199-8

M3 - Article

AN - SCOPUS:0027978622

SN - 0040-4039

VL - 35

SP - 5845

EP - 5848

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Stereoselective photocycloaddition of silyl enol ethers to aldehydes. Configurational control of three stereogenic centers in oxetanes

Abstract

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