Roux M, Santelli M, Parrain JL
Laboratoire de Synthese Organique associe au CNRS (ESA 6009), Faculte des Sciences de Saint Jerome, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.
Org Lett. 2000 Jun 15;2(12):1701-4. doi: 10.1021/ol0058137.
The (Z)-1-trimethylsilyl-3-bromopenta-2,4-diene 3 was prepared through a sequence involving the reductive silylation of butadiene, dibromocarbene addition on the resulting disilane 1, and thermolytic ring opening. With aldehydes, this new pentadienylsilane reacts exclusively via an S(E)' ' pathway. In the presence of an alcohol or a carbamate under Lewis acid activation, 3 yields, respectively, bromopentadienyl ethers or bromopentadienyl-protected amines.
(Z)-1-三甲基甲硅烷基-3-溴代戊-2,4-二烯3的制备是通过一系列反应实现的，包括丁二烯的还原硅氢化反应、所得乙硅烷1上的二溴卡宾加成反应以及热解环开环反应。这种新型戊二烯基硅烷与醛反应时仅通过S(E)' '途径进行。在路易斯酸活化下，3与醇或氨基甲酸酯反应，分别生成溴代戊二烯基醚或溴代戊二烯基保护的胺。
