Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids  

作　　者：Sankar Rao Suravarapu Bettina Peter Philippe Renaud 

机构地区：[1]Department of Chemistry and Biochemistry, University of Bern

出　　处：《Science China Chemistry》2019年第11期1504-1506,共3页中国科学（化学英文版）

基　　金：supported by the Swiss National Science Foundation(200020_172621);the University of Bern;supported by the State Secretariat for Education,Research and Innovation(SERI)via a Swiss Government Excellence Scholarships for Foreign Scholars and Artists

摘　　要：A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed.The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines.By using complementary strategies,these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5)and their conversion to a variety of indolizidine alkaloids such as coniceine,indolizidine 209D and 167B,5-epi-indolizidine 249A and monomorine has been reported in the literature.A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed. The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines. By using complementary strategies, these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5) and their conversion to a variety of indolizidine alkaloids such as coniceine, indolizidine 209 D and 167 B, 5-epi-indolizidine 249A and monomorine has been reported in the literature.

关 键 词：ALKENES carbohydrogenation RADICAL reaction CATECHOL triethylborane α-iodoesters ALLYLAMINE 

分 类 号：O62[理学—有机化学]