Lautens Mark, Schmid Gavin A, Chau Anh
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.
J Org Chem. 2002 Nov 15;67(23):8043-53. doi: 10.1021/jo025822o.
We report the application of our rhodium-catalyzed nucleophilic ring-opening methodology to unsymmetrically arene-substituted oxabenzonorbornadienes. The regioselectivity of the ring opening was investigated using a variety of nucleophiles that led to a broad selection of dihydronaphthalene products. It was found that good to excellent regioselectivities are obtained using strongly pi-donating substituents, whereas sigma-donating and electron-withdrawing functionalities have a minimal effect. Post ring-opening manipulations of functional groups in the dihydronaphthalene products were shown to give efficient access to mono- and diamine tetrahydronaphthalene building blocks.
我们报道了铑催化的亲核开环方法在不对称芳基取代的氧杂苯并降冰片二烯中的应用。使用多种亲核试剂研究了开环的区域选择性，这些亲核试剂可生成多种二氢萘产物。研究发现，使用强π供电子取代基可获得良好至优异的区域选择性，而σ供电子和吸电子官能团的影响最小。二氢萘产物中官能团的开环后操作显示可有效获得单胺和二胺四氢萘结构单元。
