Studies in cuprate rearrangement and stannylcupration: Application to the stereo- and enantiospecific synthesis of a stannyldiene C10–C15 fragment of des-epoxy-rosaramycin
作者:Valérie Fargeas、Patrick Le Ménez、Isabelle Berque、Janick Ardisson、Ange Pancrazi
DOI:10.1016/0040-4020(96)00315-8
日期:1996.5
Metallate rearrangements were performed on α-(carbamoyloxy)alkenyl stannanes 4 in high yields to prepare (±)-8a and (±)-8b via alkyl transfer but failed when stannyl and stannylvinyl transfers were attempted to give 10ab and 1ab after quenching with Mel. After we optimized conditions on dihydrofuran 13, a model study, the dihydrofuran 19 could deliver cuprate rearrangements, leading after methylation
以高收率对α-(氨基甲酰氧基)烯基锡烷4进行金属化物重排,以通过烷基转移制备(±)-8a和(±)-8b,但当尝试用苯乙烯淬灭后用苯乙烯基和苯乙烯基乙烯基转移得到10ab和1ab时失败。。在我们优化了模型研究的二氢呋喃13的条件后,二氢呋喃19可以传递铜酸盐重排,甲基化后导致苯乙烯基衍生物10和苯乙烯基二烯1丰产。设想了通过使用(E)-1,2-双(三丁基锡烷基)乙烯11的Stille Pd(0)偶联反应来合成苯乙烯基二烯的第二种方法。一种有效的方法是通过对烯炔(±)-24进行锡烷基化,从而以高收率和较高的区域和立体控制得到预期的锡烷基二烯(±)-1。