Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, United States.
Org Lett. 2011 Apr 1;13(7):1881-3. doi: 10.1021/ol200422p. Epub 2011 Mar 8.
A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.
描述了一种将苯乙烯型烯烃转化为 Rh 催化不对称氢化的优秀底物的新合成策略，通过在 2'位安装羟基取代基。该方法适用于各种 E/Z 混合物的三取代烯烃底物，生成包括（R）-托特罗定在内的有价值的苄基手性化合物。还证明，2'位的羟基可以在不损失产物对映体过量的情况下高产率地轻易去除。因此，该技术代表了一种有吸引力的替代方案，替代 Ir(P-N)催化剂体系，用于未官能化烯烃的不对称氢化。
