Asymmetric Formal Synthesis of (-)-Swainsonine by a Highly Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate

作者：Li Qing Ri; Dong Guang Ri; Park Sook Jin; Hong Yong Rae; Kim In Su; Jung Young Hoon^*

来源：European Journal of Organic Chemistry, 2013, 2013(20): 4427-4433.

DOI：10.1002/ejoc.201300308

• Synthesis design
• Nitrogen heterocycles
• Alkaloids
• Amination
• Allylation
• Diastereoselectivity

A concise asymmetric formal synthesis of (-)-swainsonine from readily available D-erythronolactone is described. The key steps include a highly diastereoselective amination of a chiral benzylic ether, which occurs with the retention of stereochemistry using chlorosulfonyl isocyanate, and a palladium-catalyzed decarboxylative N-allylation of an allyl carbamate.

• 出版日期2013-7