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Practical synthesis of optically active bicyclic oxazolidinylpiperidines, chiral building blocks for preparing 1-deoxyazasugars, from serine

✍ Scribed by Masaaki Shirai; Sentaro Okamoto; Fumie Sato

Book ID: 104261752
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 133 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00969-7

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✦ Synopsis

Optically active bicyclic oxazolidinylpiperidines la, lb, lc and ld, known chiral building blocks for preparing 1-deoxyazasugars, were synthesized in high overall yield from D-serine by a method wherein the titanium(II)-mediated intramolecular nucleophilic acyl substitution and FeC13-mediated ring enlargement of bicyclic cyclopropanols are the key reactions.

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