Bogen Stéphane, Gulea Mihaela, Fensterbank Louis, Malacria Max
Laboratoire de Chimie Organique de Synthèse associé au CNRS, Université Pierre et Marie Curie, 4, place Jussieu - Tour 44-54, Case 229, 75252 Paris Cedex 05, France.
J Org Chem. 1999 Jun 25;64(13):4920-4925. doi: 10.1021/jo9904260.
An efficient radical sequence involving a 5-exo-dig, a diastereoselective 1,5-H transfer, and a rarely observed in an all-carbon system 5-endo-trig cyclization allows the construction of cyclopentyl derivatives 2 bearing four controlled stereogenic centers from diisopropyl precursors 1. Olefins 3 were also isolated as minor side products. The effect of the acetylenic substituent Y has been investigated, and the scope and the limitations of the cascade have been delineated.
一个高效的自由基序列，包括一个5-外向-双取代、一个非对映选择性的1,5-氢转移，以及在全碳体系中很少观察到的5-内向-三取代环化反应，能够从二异丙基前体1构建出带有四个可控立体中心的环戊基衍生物2。烯烃3也作为次要副产物被分离出来。研究了炔基取代基Y的影响，并确定了该串联反应的适用范围和局限性。
