Chin. J. Org. Chem. ›› 2003, Vol. 23 ›› Issue (6): 546-549. Previous Articles     Next Articles

(R)-螺[4,5]癸-2,7-二酮的合成

姚文刚;王剑波   

  1. 北京大学化学学院生物有机
  • 发布日期:2003-06-25

Synthesis of Enantiomerically Pure (R) -Spiro[4,5] decane-2,7-dione

Yao Wengang;Wang Jianbo   

  1. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education,Department of Chemical Biology,College of Chemistry,Peking University
  • Published:2003-06-25

Starting from cyclohexenone, through catalytic asymmetric Michael addition, homologation by Wolff rearrangement, and finally Rh(II) carbene intramolecular C-H insertion, the enantiomerically pure (R)- spiro[4,5]-decane-2,7-dione was synthesized in 8 steps and 28.5% overall yield. This synthesis further confirms that Rh(n) carbene C-H insertion proceeds with complete retention of configuration.

Key words: cyclohexenone;MICHAEL ADDITION REACTION;REARRANGEMENT REACTION, CARBENE;INSERTION REACTION;spiro diketone

CLC Number: