MOM-protected 3-hydroxy-5-phenyl-isoxazole: Regioselective preparation and synthetic application

Highly regioselective (>90%) MOM-protection of 3-hydroxy-5-phenyl-isoxazole, followed by elaboration in 4-position via directed ortho-metalation and mild deprotection with cold methanolic HCl provided ready access to a series of zwitterionic isoxazole derivatives. A practical synthesis of zwitter...

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Bibliographic Details
Published in:Tetrahedron letters 1996-09, Vol.37 (38), p.6857-6860
Main Authors: Alzeer, Jawad, Nock, Nadine, Wassner, Guy, Masciadri, Raffaello
Format: Article
Language:English
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Summary:Highly regioselective (>90%) MOM-protection of 3-hydroxy-5-phenyl-isoxazole, followed by elaboration in 4-position via directed ortho-metalation and mild deprotection with cold methanolic HCl provided ready access to a series of zwitterionic isoxazole derivatives. A practical synthesis of zwitterionic 3-hydroxyisoxazoles was developed using the versatile MOM protective group
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01547-X