摘要
(-)-莰烷磺内酰胺手性助剂与巴豆酸酰氯作用生成N-反式丁烯酰基衍生物(4),进而与n-C_4H_9MgBr进行Michael加成反应,发现在CuBr·Me_2S存在下,产物以S构型为主,且化学产率明显提高。经六步合成了桃潜蛾性信息素(S)-14-甲基-1-十八碳烯(1)及其对映异构体(R)-1。
Grignard agents (n - C4H9MgBr) in the presence of CuBr - Me2S underwent 1,4 -Michael addition to N - crotonoyl - hornanesultam prepared from D - ( - ) - hornanesultam and crotonoic anhydride to give the main product of S - configuration. The sex pheromone of peach leafminer moth - (S ) - 14 - methyl - 1 - octadecene 1 and its enanliomer (R ) - 1 were prepared via six steps of readions with the optical purity being 97% and 95% , respectively.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
1999年第5期528-532,共5页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金
关键词
桃潜蛾
昆虫性信息素
不对称合成
peach leafminer moth, insect sex pheromone, ( - ) - bornane - 10, 2 - saltam, asymmetric synthesis
