Lacasse Marie-Christine, Poulard Cyril, Charette André B
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
J Am Chem Soc. 2005 Sep 14;127(36):12440-1. doi: 10.1021/ja0529687.
A new family of zinc carbenoids derived from phosphoric acids was developed and used in the cyclopropanation of allylic alcohols and ethers and also of unfunctionalized olefins. The use of the chiral phosphoric acid of a 3,3'-disubstituted BINOL leads to efficient stereocontrol, affording the cyclopropanes of allylic and homoallylic ethers with complete conversions and up to 93% ee. A catalytic version of this reaction using 10 mol % of the chiral phosphate reagent is also disclosed.
开发了一类源自磷酸的新型锌卡宾，并将其用于烯丙醇、醚以及未官能化烯烃的环丙烷化反应。使用3,3'-二取代联萘酚的手性磷酸可实现高效的立体控制，能以完全转化且高达93%的对映体过量（ee）得到烯丙基醚和高烯丙基醚的环丙烷产物。还公开了使用10 mol%手性磷酸试剂的该反应的催化版本。
