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Stereoselective Synthesis of (–)‐α‐Conhydrine and Its Pyrrolidine Analogue
Author(s) -
Dong Guang Ri,
Hong Seungmin,
Kim Seung In,
Kim In Su,
Jung Young Hoon
Publication year - 2012
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.201200489
Subject(s) - pyrrolidine , chemistry , stereoselectivity , regioselectivity , isocyanate , ether , alcohol , stereochemistry , organic chemistry , catalysis , polyurethane
The stereoselective synthesis of (–)‐α‐conhydrine and its pyrrolidine analogue was achieved from readily available D ‐erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2‐ anti ‐dibenzyl ether to afford the 1,2‐ anti ‐amino alcohol.