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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.