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

doi:10.1055/s-1999-2589

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

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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

Abstract

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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.

3,4-dehydroproline - 3-pyrroline - aziridine - thermodynamic equilibration

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