A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes

作者：Zhang Hong Kui^*; Xu Shou Qiang; Zhuang Jia Jia; Ye Jian Liang; Huang Pei Qiang

来源：Tetrahedron, 2012, 68(33): 6656-6664.

DOI：10.1016/j.tet.2012.06.006

A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from D-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a-e and 9h-j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65-91%. These reductive hydroxyalkylations are highly diastereoselective in establishing the C-4 stereogenic center. By this way, the asymmetric syntheses of (-)-8a-epi-swainsonine (4) and (-)-8,8a-di-epi-swainsonine (5) have been achieved.

• 出版日期2012-8-19
• 单位厦门大学