The Mitsunobu reaction of ortho-ethers of secondary benzylic alcohols. Concise enantioselective synthesis of a key intermediate of the novel β-adrenergic receptor antagonist MY336-a
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...
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Published in | Tetrahedron letters Vol. 37; no. 30; pp. 5329 - 5332 |
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Main Author | |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
22.07.1996
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | 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 β-adrenergic receptor antagonist MY336-a was achieved exploiting this observation.
Virtually complete Mitsunobu inversion is achieved for R
1= Me, Bn when R
2= MeO. Partial racemization of the 4-nitrobenzoate ester (PNB) is observed when R= H. This allowed the enantioselective synthesis of
1. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/0040-4039(96)01122-7 |