Regio-and diastereoselective ene reaction of 4-phenyl-1, 2, 4-triazoline-3, 5-dione with chiral allylic alcohols and their derivatives

…, GL Lin, BJ Uang, FL Liao, SL Wang

Index: Gau, Ay-Hua; Lin, Guey-Liang; Uang, Biing-Jiun; Liao, Fen-Ling; Wang, Sue-Lein Journal of Organic Chemistry, 1999 , vol. 64, # 7 p. 2194 - 2201

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Citation Number: 26

Abstract

Chiral allylic alcohols 1a-e reacted with 4-phenyl-1, 2, 4-triazoline-3, 5-dione (PTAD) in CH2Cl2 to produce 3-amino-1-alken-4-ols 2 and 3 in 78-89% yields, with 68-90% diastereomeric excess (de) in favor of the threo isomer. Chiral allylic ethers 1f, g and acetates 1h, i gave similar yields but lower de (34-66%). Reaction of allylic alcohols 6a-e with PTAD in CH2Cl2 produced 1, 3-regioisomers 7 and 8 exclusively in 33-65% yields ...