Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence

Thorsten Bach

doi:10.1016/S0040-4039(00)73179-0

Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence

Thorsten Bach

University of Münster

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

21 Scopus citations

Abstract

It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paternò-Büchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.

Original language	English
Pages (from-to)	1855-1858
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(00)73179-0
State	Published - 21 Mar 1994
Externally published	Yes

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@article{41bcaa156d0f44fc95e5337c0d4db851,

title = "Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence",

abstract = "It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Patern{\`o}-B{\"u}chi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.",

author = "Thorsten Bach",

note = "Funding Information: Acknowledgements. This work was generously supported by the Deutiche Forschungs-gemeimchaft (Ba 1372/l-L). by the Gesellschajl zur F\&derung der Westfllischen WiZZzeZ?rrs- Universifflt and by the Fends der Chetischen Zndustrie. I would like to thank S. Marose for technical assistance and Pros Dr. D. Hoppe for his constant encouragement and support.",

year = "1994",

month = mar,

day = "21",

doi = "10.1016/S0040-4039(00)73179-0",

language = "English",

volume = "35",

pages = "1855--1858",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "12",

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TY - JOUR

T1 - Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence

AU - Bach, Thorsten

N1 - Funding Information: Acknowledgements. This work was generously supported by the Deutiche Forschungs-gemeimchaft (Ba 1372/l-L). by the Gesellschajl zur F&derung der Westfllischen WiZZzeZ?rrs- Universifflt and by the Fends der Chetischen Zndustrie. I would like to thank S. Marose for technical assistance and Pros Dr. D. Hoppe for his constant encouragement and support.

PY - 1994/3/21

Y1 - 1994/3/21

N2 - It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paternò-Büchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.

AB - It has been shown that enol ether derived 2-phenyl-3-silyloxy-oxetanes 1 and 3 can be cleaved by catalytic hydrogenation. In combination with the preceding Paternò-Büchi reaction the method enables a regioselective access to 1,2-diols 2 starting from olefinic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.

UR - https://www.scopus.com/pages/publications/0028203756

U2 - 10.1016/S0040-4039(00)73179-0

DO - 10.1016/S0040-4039(00)73179-0

M3 - Article

AN - SCOPUS:0028203756

SN - 0040-4039

VL - 35

SP - 1855

EP - 1858

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence

Abstract

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