期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 350, 期 16, 页码 2467-2472出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800430
关键词
aldol reaction; asymmetric catalysis; organocatalysis; prolinethioamides; solvent-free reactions
资金
- Generalitat Valenciana [GRMECUPOS05111, GV051144, GV120071142]
- [CTQ2004-00808/BQQ]
- [CTQ2007-62771/BQU]
- [INGENIO 2010 CSD2007-00006]
A solvent-free asymmetric and direct anti-aldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by recyclable L-proline-amides and L-prolinethioarnides 3 is studied. The L-prolinethioamide 3d (5 mol%), derived from L-Pro and (R)-1-aminoindane, is the most efficient catalyst for this process affording the anti-aldol adducts in high yields with excellent diastereo- and enantio-selectivities (up to > 98/2 dr, up to 98% ee) at 0 degrees C or room temperature. Prolinethioamide 3d is an effective organocatalyst for the first asymmetric, solvent-free, intramolecular Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to reported catalysts in organic solvents. Moreover, organocatalyst 3d can be easily recovered and reused by a simple acid/base extraction.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据