Synlett 1999; 1999(2): 228-230
DOI: 10.1055/s-1999-2589
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.

Selective Synthesis of Nonracemic 3-Pyrrolines and 2,3-cis-2-Vinylaziridines from (Z)-Amino Allylic Alcohols: A New Synthetic Route to Chiral 3,4-Dehydroproline

Kiyonori Ishii* , Hiroaki Ohno, Yoshiji Takemoto, Toshiro Ibuka
  • *Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan; Fax +81-75-7 53-45 69; E-mail: tibuka@pharm.kyoto-u.ac.jp
Further Information

Publication History

Publication Date:
31 December 1999 (online)

Both nonracemic 3-pyrrolines and 2,3-cis-2-vinylaziridines have been synthesized selectively from common (Z)-allylic alcohols by simply changing the leaving group and the reaction conditions. Whereas treatment of (Z)-allylic mesylates with NaH yields exclusively 3-pyrrolines in high yields, exposure of allylic methyl carbonates to a catalytic amount of Pd(PPh3)4 affords 2,3-cis-2-vinylaziridines diastereoselectively in high yields. A simple synthesis of (S)-3,4-dehydroproline starting from (R)-serine is also described.