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A Straightforward Synthesis of Enantiopure Bicyclic Azetidines
Author(s) -
Sivaprakasam Mangaleswaran,
Couty François,
David Olivier,
Marrot Jérôme,
Sridhar Regati,
Srinivas Boga,
Rama Rao Kakulapati
Publication year - 2007
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.200700616
Subject(s) - enantiopure drug , azetidine , chemistry , bicyclic molecule , nucleophile , alkylation , ring (chemistry) , intramolecular force , enantioselective synthesis , heptane , aziridine , organic chemistry , stereochemistry , combinatorial chemistry , catalysis
Enantiomerically pure 1‐azabicyclo[3.2.0]heptane derivatives were synthesized in a straightforward manner from readily available chiral sources, namely, enantiomerically pure epoxides and L ‐proline. The key step of this synthesis relied on a diastereoselective intramolecular alkylation of a proline enolate, which led to an azetidine ring fused to a five‐membered ring. These strained bicyclic nitrogen derivatives were found to be good precursors for the preparation of azepanes, after transformation into the corresponding ammonium trifluoromethanesulfonates followed by reaction with nucleophiles.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)