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Synthesis and rearrangement of silylated oxy-cope systems


Koch-Huber, P; Kunz, R W; Bienz, Stefan (1999). Synthesis and rearrangement of silylated oxy-cope systems. Molecules Online, 3(2):9-19.

Abstract

Addition of allyl or vinyl organometallic reagents to chiral a,b- or b,g-unsaturated acylsilanes afforded stereoselectively 3-silylated 3-hydroxy-1,5-dienes that are stereoselectively converted to d,e-unsaturated acylsilanes by the thermal oxy-Cope rearrangement. The rearrangement is restricted to compounds possessing an (alkoxy)methyl substituent at the silicon moiety; upon heating, analogous compounds with the t-BuMe2Si group in the 3-position led to decomposition only. The (alkoxy)methyl group at silicon is supposed to act as a weak internal base, which accelerates the rearrangment reaction.

Abstract

Addition of allyl or vinyl organometallic reagents to chiral a,b- or b,g-unsaturated acylsilanes afforded stereoselectively 3-silylated 3-hydroxy-1,5-dienes that are stereoselectively converted to d,e-unsaturated acylsilanes by the thermal oxy-Cope rearrangement. The rearrangement is restricted to compounds possessing an (alkoxy)methyl substituent at the silicon moiety; upon heating, analogous compounds with the t-BuMe2Si group in the 3-position led to decomposition only. The (alkoxy)methyl group at silicon is supposed to act as a weak internal base, which accelerates the rearrangment reaction.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1999
Deposited On:12 Sep 2017 15:30
Last Modified:09 Dec 2017 02:13
Publisher:Springer
ISSN:1433-1373

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