摘要
以反式肉桂醇为原料,经Sharpless不对称环氧化,产生所需的两个手性碳(2S,3S)后,产物经氧化、酯化即得标题产 物(-)-(2R,3S)-3-苯基-2,3-环氧丙酸甲酯(1),三步总收率28.4％,所得产物的ee值>95％。
Asymmetric synthesis of ( - ) - (2R,3S) - 3 - phenyl - 2,3 - epoxymethylpropionate ( 1 ) by scheme 1 was described. Trans-cinnamyl alcohol was selected as a starting material, sharpless asymmetric epoxydation of tans-cinnamyl alcohol can be carried out in the presence of t-butyl hydroperoxide, using ( + ) - diethyl tartrate as the asymmetric adjuvant, to produce two desired chiral centers(2S,3S). The title product ( - ) - (2R,3S) -3 -phenyl -2,3 -epoxymethylpropionate was obtained by successive oxidation and esterification with the overall of 28.4% ( ee >95% ).
出处
《广东药学院学报》
CAS
2004年第2期97-98,共2页
Academic Journal of Guangdong College of Pharmacy
