A Practical Method for the Separation of E/Z-Isomeric Silyl Enol Ethers by Kinetic Resolution

Claudia Hippeli; Nils Basso; Franziska Dammast; Hans-Ulrich Reißig

doi:10.1055/s-1990-26776

Synthesis 1990; 1990(1): 26-27
DOI: 10.1055/s-1990-26776

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A Practical Method for the Separation of E/Z-Isomeric Silyl Enol Ethers by Kinetic Resolution

Claudia Hippeli^* , Nils Basso, Franziska Dammast, Hans-Ulrich Reißig

^*Institut für Organische Chemie der Technischen Hochschule, Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Federal Republic of Germany

Abstract

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E/Z-Isomeric silyl enol ethers 1 (1-trimethylsiloxy-1-alkenes) can be separated by cycloaddition to nitrosostyrene (2), which allows recovery of unconsumed isomerically pure (Z)-1. On the other hand, the high selectivity of diphenylketene (5) can be exploited to trap Z silyl enol ethers and to reisolate pure (E)-1. The simple procedures make available gram quantities of both isomers in pure state.

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