The β-silicon effect as a control element for the regioselective ring opening of oxetanes

Thorsten Bach; Kristian Kather

doi:10.1016/S0040-4020(01)89541-7

The β-silicon effect as a control element for the regioselective ring opening of oxetanes

Thorsten Bach
, Kristian Kather

University of Münster

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

24 Scopus citations

Abstract

The title compounds 5 was prepared by a stereoselective photocycloaddition of silyl enol ether 9 and benzaldehyde. In Lewis- and Brönsted-acid promoted ring opening reactions the oxetane is selectively cleaved to yield a 1,2-diol 6 which cyclizes under the reaction conditions to the dihydrofuran 11. The constitution of the final product was elucidated by reductive to the alcohol 14.

Original language	English
Pages (from-to)	12319-12328
Number of pages	10
Journal	Tetrahedron
Volume	50
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4020(01)89541-7
State	Published - 1994
Externally published	Yes

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title = "The β-silicon effect as a control element for the regioselective ring opening of oxetanes",

abstract = "The title compounds 5 was prepared by a stereoselective photocycloaddition of silyl enol ether 9 and benzaldehyde. In Lewis- and Br{\"o}nsted-acid promoted ring opening reactions the oxetane is selectively cleaved to yield a 1,2-diol 6 which cyclizes under the reaction conditions to the dihydrofuran 11. The constitution of the final product was elucidated by reductive to the alcohol 14.",

author = "Thorsten Bach and Kristian Kather",

year = "1994",

doi = "10.1016/S0040-4020(01)89541-7",

language = "English",

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pages = "12319--12328",

journal = "Tetrahedron",

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T1 - The β-silicon effect as a control element for the regioselective ring opening of oxetanes

AU - Bach, Thorsten

AU - Kather, Kristian

PY - 1994

Y1 - 1994

N2 - The title compounds 5 was prepared by a stereoselective photocycloaddition of silyl enol ether 9 and benzaldehyde. In Lewis- and Brönsted-acid promoted ring opening reactions the oxetane is selectively cleaved to yield a 1,2-diol 6 which cyclizes under the reaction conditions to the dihydrofuran 11. The constitution of the final product was elucidated by reductive to the alcohol 14.

AB - The title compounds 5 was prepared by a stereoselective photocycloaddition of silyl enol ether 9 and benzaldehyde. In Lewis- and Brönsted-acid promoted ring opening reactions the oxetane is selectively cleaved to yield a 1,2-diol 6 which cyclizes under the reaction conditions to the dihydrofuran 11. The constitution of the final product was elucidated by reductive to the alcohol 14.

UR - https://www.scopus.com/pages/publications/0028116883

U2 - 10.1016/S0040-4020(01)89541-7

DO - 10.1016/S0040-4020(01)89541-7

M3 - Article

AN - SCOPUS:0028116883

SN - 0040-4020

VL - 50

SP - 12319

EP - 12328

JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

The β-silicon effect as a control element for the regioselective ring opening of oxetanes

Abstract

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