Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6.
Org Lett. 2010 Dec 3;12(23):5418-21. doi: 10.1021/ol1022239. Epub 2010 Nov 2.
Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH(4)BF(4) to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.
手性催化剂控制的外消旋氧杂双环烯烃的不对称开环反应得到两种易于分离的非对映异构体产物，ee 值都很高。需要使用带有 NH(4)BF(4)添加剂的阳离子 Rh 催化剂来调节反应性，以获得具有合成用途的产率。通过将每种取代的氨基四氢萘产物转化为不同的生物相关分子，以高效和实用的方式展示了它们的用途。
