An organocatalytic approach to stereoselective synthesis of 2-hydroxyazetidines and 2-hydroxypyrrolidines

作者：Rai Ankita; Yadav La Dhar S^*

来源：Tetrahedron Letters, 2013, 54(24): 3127-3131.

DOI：10.1016/j.tetlet.2013.04.013

• 2-Hydroxyazetidines
• 2-Hydroxypyrrolidines
• Organo-catalysis
• Aziridine ring-opening
• Stereoselective synthesis

A straightforward asymmetric synthesis of a new series of 2-hydroxyazetidines/2-hydroxypyrrolidines with excellent diastereoselectivity was developed via enamine catalysis using diphenylprolinol silyl ether. The Mannich-type reaction of chiral enamines with various aldimines/aziridines under mild conditions followed by intramolecular hemiaminalization affords the desired products 2-hydroxyazetidines and 2-hydroxypyrrolidines, respectively, in a one-pot operation. The scope and generality of the reaction was adequately investigated and the conditions were optimized extensively.

• 出版日期2013-6-12