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Catalytic Enantioselective Synthesis of 3,4,5‐Trisubstituted Isoxazoline N ‐Oxides and Regioselective Synthesis of 3,4,5‐Trisubstituted Isoxazoles
Author(s) -
Sahoo Subas Chandra,
Pan Subhas Chandra
Publication year - 2019
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.201801693
Subject(s) - regioselectivity , chemistry , enantioselective synthesis , isoxazole , catalysis , thiourea , aryl , combinatorial chemistry , cycloaddition , organic chemistry , alkyl
An efficient catalytic asymmetric synthesis of 3,4,5‐trisubstituted isoxazoline N ‐oxides and regioselective synthesis of 3,4,5‐trisubstituted isoxazoles has been described. α‐Nitrocinnamates and α‐nitrobenzophenones were utilized as Michael acceptors respectively. Hydroquinine derived thiourea in combination with cesium carbonate was effective for the synthesis of isoxazoline N ‐oxides whereas stoichiometric di ‐isopropylethylamine (DIPEA) was the best choice for isoxazole synthesis. In both cases a range of aryl and heteroaromatic groups was tolerated.