Hetero Diels-Alder Reactions of Optically Active Enol Ethers with a Nitrosoalkene: Asymmetric Synthesis of 1, 2-Oxazine Derivatives

Thomas Arnold; Hans-Ulrich Reissig

doi:10.1055/s-1990-21147

Synlett 1990; 1990(9): 514-516
DOI: 10.1055/s-1990-21147

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Hetero Diels-Alder Reactions of Optically Active Enol Ethers with a Nitrosoalkene: Asymmetric Synthesis of 1, 2-Oxazine Derivatives

Thomas Arnold^* , 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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α-Nitrosostyrene (2) cycloadds to optically active vinyl ethers 1 or (Z)- and (E)-1-propenyl ethers 5, incorporating chiral auxiliaries (menthyl, 8-phenylmenthyl, or bornane derivatives), to afford 6-alkoxy-5,6-dihydro-4H-1,2-oxazines 3 and 6 with moderate to excellent diastereoselectivities. Also, an efficient two-step synthesis of optically active (Z)- and (E)-1-propenyl ethers 5 is described.

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