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A Single‐Step Synthesis of 4‐Oxazolin‐2‐ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters
Author(s) -
Santoyo Blanca M.,
GonzálezRomero Carlos,
Merino Omar,
MartínezPalou Rafael,
FuentesBenites Aydeé,
JiménezVázquez Hugo A.,
Delgado Francisco,
Tamariz Joaquín
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.200900114
Subject(s) - stereocenter , chemistry , nucleophile , electrophile , bromide , organic chemistry , combinatorial chemistry , condensation , enantioselective synthesis , catalysis , physics , thermodynamics
A new method for the synthesis of 4‐oxazolin‐2‐ones by a one‐pot MW‐promoted condensation of α‐ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)