Department of Chemistry, The Scripps Research Institute, 130 Scripps Way, 3A2, Jupiter, FL 33458, USA.
Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8703-7. doi: 10.1002/anie.201302535. Epub 2013 Jul 1.
An efficient and highly enantio- and diastereoselective synthesis of propionamide aldols is described. Formation of the -enolborinate via the hydroboration of 4-acryloylmorpholine with (diisopinocampheyl)borane followed by aldol reactions with representative achiral and chiral aldehydes provided -α-methyl-β-hydroxy morpholine carboxamides with excellent enantio- and diastereoselectivity (96–98% ee and d.r. >20:1).
本文描述了一种高效、高对映选择性和非对映选择性合成丙酰胺醇的方法。通过(二异松蒎基)硼烷对 4-丙烯酰基吗啉进行硼氢化反应,形成 -烯醇硼酸酯,然后与代表性的手性和非手性醛进行醛醇反应,得到了 -α-甲基-β-羟基吗啉羧酸酰胺,具有优异的对映选择性和非对映选择性(96-98%ee 和 d.r. >20:1)。