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Synthesis of Enantiopure 2‐Aryl(Alkyl)‐2‐trifluoromethyl‐Substituted Morpholines and Oxazepanes
Author(s) -
nenmacher Jean,
Grellepois Fabienne,
Portella Charles
Publication year - 2009
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.200900387
Subject(s) - enantiopure drug , chemistry , trifluoromethyl , alkyl , aryl , ether , halogenation , stereochemistry , williamson ether synthesis , organic chemistry , enantioselective synthesis , catalysis
The synthesis of morpholines and oxazepanes derivatives containing a trifluoromethyl group on a quaternary carbon has been achieved from a common enantiopure O ‐allyl amino ether precursor. Classic 6‐ exo iodoamination provided the iodomorpholines, versatile synthetic intermediates, whereas a hydrozirconation/iodination sequence allowed the synthesis of oxazepanes by a 7‐ endo cyclisation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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