Dipartimento di Chimica Organica e Industriale-Universita' degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy.
Org Biomol Chem. 2011 Feb 7;9(3):739-43. doi: 10.1039/c0ob00570c. Epub 2010 Nov 17.
A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.
发展了一种高对映选择性的三氯硅烷介导的 N-苄基烯胺还原反应；廉价、易于制备的无金属催化剂与廉价的手性助剂相结合，使得该反应可以在具有不同结构特征的底物上进行，通常可以完全控制立体选择性。通过容易的氢化脱保护作用，随后将β-氨基酯转化为 2-氮杂环丁酮，成功地完成了对映体纯的β-内酰胺（>98%ee）的合成。
