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Regio- and Diastereoselective Ene Reaction of Triazolinedione with Vinylsilanes

โœ Scribed by Adam, Waldemar ;Richter, Markus

Publisher
Wiley (John Wiley & Sons)
Year
1992
Tongue
English
Weight
402 KB
Volume
125
Category
Article
ISSN
0009-2940

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โœฆ Synopsis

Ene reaction / Manes, vinyl-/ Triazolinediones / Cycloaddition / Regioselectivity / Diastereoselectivity

The ene reaction of 4-methyl-l,2,4-triazoline-3,5-dione stereoselectivity. For the former we invoke preferential clea-(MTAD) with vinylsilanes 1 has been investigated. In all cases vage of the C -N bond proximate to the silyl substituent on studied, only hydrogen abstraction geminal to the silyl group the aziridine ring, for the latter steric repulsion between the with formation of triazolidinediones 3 occurred, irrespective adjacent silyl and alkyl group controls the observed E-type of the number and size of the substituents at the double bond. stereochemistry. A new synthetic approach to the trisubsti-A mechanism with an aziridinium imide as intermediate is tuted vinylsilane l e based on reductive lithiation of the corproposed to explain the observed regioselectivity and dia-responding vinyl sulfide is described.

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