Kudoh Takayuki, Ishikawa Teruhiko, Shimizu Yoshihiro, Saito Seiki
Department of Bioscience and Biotechnology, School of Engineering and School of Education, Okayama University, Tsushima, Okayama, Japan 700-8530.
Org Lett. 2003 Oct 16;5(21):3875-8. doi: 10.1021/ol035423v.
[reaction: see text] A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et(3)N in CH(3)CN at 0 degrees C to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2] cycloaddition reaction. Some examples for transforming the cycloadducts to amino polyols are also presented.
[反应：见正文] 描述了一种将2-硝基链烷醇转化为立体定向氨基多元醇前体的方法。2-硝基链烷醇羟基的二苯基乙烯基硅烷化，随后在0℃至室温下于乙腈中使用TMS-Cl和Et(3)N生成硅基硝酮酯，通过立体选择性分子内硝酮酯-烯烃[3 + 2]环加成反应生成稠合双环杂环。还给出了一些将环加成产物转化为氨基多元醇的实例。
