Acta Chimica Sinica ›› 2001, Vol. 59 ›› Issue (4): 587-593. Previous Articles     Next Articles

Original Articles

新型手性方酸衍生物的合成及催化前手性芳酮的不对称 还原反应

吕守茂;周海兵;谢如刚;周忠远;陈新滋;杨登贵   

  1. 四川大学化学系.成都(610064);香港理工大学手性技术开放实验室与应用生物 和化学科技系;台湾省中兴大学化学系
  • 出版日期:2001-04-15 发布日期:2001-04-15

Study on the synthesis of new chiral derivatives of squaric acid and their application in asymmetric catalytic borane reduction of prochiral aryl ketones

Lu Shoumao;Zhou Haibing;Xie Rugang;Zhou Zhongyuan;Chen Xinzi;Yang Denggui   

  1. Sichuan Univ, Dept Chem.Chengdu(610064)
  • Online:2001-04-15 Published:2001-04-15

Eleven new chiral squaric aicd amidoalcohols bave been synthesized by reaction of alkyl amines or thiols with 3-butoxy-[(1'S,2'R)-(2' hydroxy-1',2'-diphenylethyl) amino]-3-cyclobutene-1,2-dione, which is prepared by the reaction of (1R, 2S)-2-amino-1,2-diphenylalcohol with dibutyl squrate. The in situ formed chiral oxazaborolidines have been used in the enantioselective borane reduction of prochiral ketones to afford the alcohol products in a range 88%~98% yield and 42% ~81% enantiomeric excesses, respectively. All of the new compounds are confirmed by IR, 1^H NMR, MS and element analysis, in which compound 4b is also confirmed by X-ray analysis.

Key words: SQUARIC ACID, KETONE, REDUCTION, AMINO ALCOHOL, BORANES

CLC Number: