Boyce Gregory R, Johnson Jeffrey S
Department of Chemistry and Physics, Florida Gulf Coast University , Fort Myers, Florida 33965, United States.
Department of Chemistry, University of North Carolina , Chapel Hill, North Carolina 27599-3290, United States.
J Org Chem. 2016 Feb 19;81(4):1712-7. doi: 10.1021/acs.joc.5b02693. Epub 2016 Feb 2.
A diastereoselective auxiliary-mediated vinylation/[1,2]-Brook rearrangement/vinylogous Michael cascade of silyl glyoximide, vinylmagnesium bromide, and nitroalkenes is described. The reaction occurs with complete regio- and diastereocontrol in good yield. The diastereoselectivity is induced by a rare instance of 1,7-chirality transfer that is hypothesized to arise from a trans-multihetero-decalin transition state.
描述了一种非对映选择性辅助剂介导的甲硅烷基乙二酰亚胺、乙烯基溴化镁和硝基烯烃的乙烯基化/[1,2]-布鲁克重排/乙烯型迈克尔串联反应。该反应以良好的收率在完全区域和非对映控制下发生。非对映选择性是由罕见的1,7-手性转移实例诱导的，据推测这是由反式多杂十氢化萘过渡态引起的。
