Asymmetric Formal Synthesis of (–)‐Swainsonine by a Highly Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate | Zendy

Li Qing Ri | Zendy; Dong Guang Ri | Zendy; Park Sook Jin | Zendy; Hong Yong Rae | Zendy; Kim In Su | Zendy; Jung Young Hoon | Zendy

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

Author(s) -

Li Qing Ri,

Dong Guang Ri,

Park Sook Jin,

Hong Yong Rae,

Kim In Su,

Jung Young Hoon

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300308

Subject(s) - chemistry , amination , regioselectivity , allylic rearrangement , carbamate , isocyanate , swainsonine , organic chemistry , enantioselective synthesis , hydroboration , formal synthesis , catalysis , polyurethane

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.

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