通过钯催化的5-烯基噻唑酮的[3 + 2]环化反应实现季碳立体中心的高度化学选择性和非对映选择性构建。
Highly Chemo- and Diastereoselective Construction of Quaternary Stereocenters through Palladium-Catalyzed [3 + 2] Cyclization of 5-Alkenyl Thiazolones.
作者信息
Liu Yue, Huang Qian-Wei, Li Qing-Zhu, Leng Hai-Jun, Dai Qing-Song, Zeng Rong, Liu Yan-Qing, Zhang Xiang, Han Bo, Li Jun-Long
机构信息
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics , Chengdu University , Chengdu 610052 , China.
School of Pharmacy , Chengdu University of Traditional Chinese Medicine , Chengdu , 611137 , China.
出版信息
Org Lett. 2019 Sep 20;21(18):7478-7483. doi: 10.1021/acs.orglett.9b02781. Epub 2019 Sep 6.
We report a highly chemo- and diastereoselective [3 + 2] cyclization of vinylethylene carbonates and 5-alkenyl thiazolones through palladium catalysis. The previously inert aza-thioester moiety on the thiazolone substrates is reacted selectively with the zwitterionic π-allylpalladium species. A variety of amide monothioacetals (AMTA) with two quaternary stereocenters are facilely synthesized. An additional spirocyclic quaternary stereocenter could be further installed by Rh-catalyzed metal-carbene insertion into the C-S bond on the AMTA moiety in a highly stereoselective manner.
我们报道了通过钯催化实现的碳酸乙烯基酯与5-烯基噻唑酮的高度化学选择性和非对映选择性[3+2]环化反应。噻唑酮底物上先前惰性的氮杂硫酯部分与两性离子π-烯丙基钯物种发生选择性反应。轻松合成了多种具有两个季碳立体中心的酰胺单硫缩醛（AMTA）。通过铑催化的金属卡宾以高度立体选择性的方式插入AMTA部分的C-S键中，还可以进一步引入一个额外的螺环季碳立体中心。
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