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Regioselective carbohydroxylation of enol ethers by a photocycloaddition-hydrogenation sequence

✍ Scribed by Thorsten Bach

Book ID
104214403
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
256 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

Abatraet: 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 Patemb-Btichi reaction the method enables a regioselective access to 1,2diols 2 starting from oleftic substrates. Optionally, the reduction of 3 can be conducted such that the more hindered tertiary alcohol site in 2 remains silyl-protected.

In the course of the Patemb-Btichi reaction an alkene is converted photochemically to an oxetane ring.' As result of the transformation one carbon of the former double bond bears an oxygen atom and the other carbon is connected to an alkyl group. In certain cases it has been observed that

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