Asymmetric Formal Synthesis of (–)‐Swainsonine by a Highly Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. Issue 20 (31st May 2013)

• Record Type: Journal Article
• Authors: Li, Qing Ri; Dong, Guang Ri; Park, Sook Jin; Hong, Yong Rae; Kim, In Su; Jung, Young Hoon
• Is Part Of: European journal of organic chemistry. Issue 20(2013)
• Page Start: 4427
• Page End: 4433
• Publication Date: 2013-05-31
• Subjects: Synthesis design -- Nitrogen ­heterocycles -- Alkaloids -- Amination -- ­Allylation -- Diastereoselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300308
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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.