Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
J Org Chem. 2010 Jun 18;75(12):4056-68. doi: 10.1021/jo100391e.
A highly enantioselective desymmetrization of meso cyclopent-2-ene-1,4-diethyl dicarbonates has been developed using a Rh-catalyzed asymmetric allylic substitution. Depending on the type of ligand used, each of two regioisomeric products can be obtained in good yield and excellent enantioselectivity. Under rhodium(I) catalysis, bisphosphine P-Phos ligands form trans-1,2-arylcyclopentenols as the major product, whereas Segphos ligands lead predominantly to trans-1,4-arylcyclopentenols.
已开发出一种使用 Rh 催化的不对称烯丙基取代反应，对消旋环戊-2-烯-1,4-二乙酯二碳酸酯进行高对映选择性去对称化反应。根据所使用配体的类型，可以以良好的收率和优异的对映选择性获得两种区域异构体产物中的每一种。在铑（I）催化下，双膦 P-Phos 配体形成顺式-1,2-芳基环戊烯醇作为主要产物，而 Segphos 配体则主要得到顺式-1,4-芳基环戊烯醇。
