Preparation and use of chiral (Z)-enol ethers in asymmetric bradsher cycloaddition
作者:Olivia Sageot、Daphnée Monteux、Yves Langlois、Claude Riche、Angèle Chiaroni
DOI:10.1016/0040-4039(96)01540-7
日期:1996.9
Chiral (Z)-enol ethers 7a-7p have been prepared in two steps. Bradsher cycloaddition between such compounds and 2,7-naphthyridinium salt 4b in water or in ter-butanol-water afforded, in some cases with good yield and diastereoselectivity, highly functionalized isoquinoline derivatives, potential intermediates in Manzamine A 1 total synthesis. X-Ray analysis secured the direction of asymmetric induction
分两步制备了手性(Z)-烯醇醚7a-7p。在水或叔丁醇-水中,此类化合物与2,7-萘啶鎓盐4b之间的Bradsher环加成反应在某些情况下提供了良好的收率和非对映选择性,高度官能化的异喹啉衍生物以及Manzamine A 1总合成中的潜在中间体。X射线分析确定了烯醇醚7l的不对称诱导方向。