通过对映选择性单氢化作用来对中间环状酰亚胺进行去对称化。
Desymmetrization of meso-cyclic imides via enantioselective monohydrogenation.
机构信息
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
出版信息
J Am Chem Soc. 2010 Sep 22;132(37):12832-4. doi: 10.1021/ja105783u.
meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88-97% ee using trans-[Ru((R)-BINAP)(H)(2)((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup- and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.
介环酰胺在[Ru((R)-BINAP)(H)(2)((R,R)-dpen)]和相关化合物作为催化剂，在 THF 中加入碱的条件下，被单氢化为相应的羟基内酰胺，ee 值为 88-97%。该氢化反应具有高对映体和化学选择性，是一个去对称化反应，在一个反应中形成多达五个手性中心。将羟基内酰胺转化为相应的亚氨基离子，然后加入茚，将手性中心的数量从 5 个增加到 7 个。
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