The Mitsunobu Reaction of Ortho-Ethers of Secondary Benzylic Alcohols - Concise Enantioselective Synthesis of a Key Intermediate of the Novel Beta-Adrenergic-Receptor Antagonist-My336-A

KAUFMAN, TS

TETRAHEDRON LETTERS

Elsevier

Lugar: Amsterdam; Año: 1996 vol. 37 p. 5329 - 5332

Chiral secondary benzylic alcohols bearing an ortho-alkoxy substituent suffer ring-assisted racemization during the Mitsunobu reaction; however, their congeners bearing also a 3-substituent undergo virtually complete Mitsunobu inversion. A concise enantioselective synthesis of a key intermediate of the beta-adrenergic receptor antagonist MY336-a was achieved exploiting this observation.