Download PDF
Synlett 1990; 1990(9): 514-516
DOI: 10.1055/s-1990-21147
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.