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Enantioselective Alkylative Double Ring Opening of Epoxides: Synthesis of Enantioenriched Unsaturated Diols and Amino Alcohols
Author(s) -
Hodgson David M.,
Maxwell Christopher R.,
Miles Timothy J.,
Paruch Edyta,
Stent Matthew A. H.,
Matthews Ian R.,
Wilson Francis X.,
Witherington Jason
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20021115)41:22<4313::aid-anie4313>3.0.co;2-b
Subject(s) - enantioselective synthesis , carbenoid , chemistry , alcohol , lithium (medication) , epoxide , ring (chemistry) , intermolecular force , diol , organic chemistry , stereochemistry , catalysis , molecule , rhodium , medicine , endocrinology
Enantioselective generation and intermolecular trapping of a lithium carbenoid occurs in the reaction of epoxides of 2,5‐dihydrofuran, 2,5‐dihydropyrrole, and oxa‐ and aza‐bicyclo[ n. 2.1]alkenes ( n =2, 3) with organolithium compounds in the presence of external chiral ligands. This methodology leads to the synthesis of important unsaturated diol and amino alcohol functionality (see scheme; tert ‐butoxycarbonyl).