以(S)-4-苄基-2-噻唑硫酮为手性助剂,与丁烯酰氯进行N-酰化反应,所得酰化产物与溴代正丁烷的铜试剂进行不对称迈克尔加成反应,在NaBH4作用下解脱得到(R)-3-甲基庚醇,再经氰化、水解等反应,合成出椰树犀牛甲虫聚集信息素,其化学总产率为39.45%,光学异构体纯度达93%e.e.以上。
(S)-4-benzylthiazolidine-2-thione, used as chiral auxiliary, was N-acylated by crotonyl chloride,and asymmetrically Michael reaction with 1-bromobutane, followed by cleavage using NaBH4 to give(R)-3-methylheptan-l-ol, which ordinally proceeded cyanidation, hydrolysis, etc to successfully synthesize the aggregation pheromone of rhinoceros beetles.The enantiomeric exess of the total synthesis is over 93% e. e. and the total yield was up to 39.45%.