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Highly Selective Synthesis of a 2-Deoxyxylonolactam via Enantioselective Carbon-Hydrogen Insertion Reactions Using Chiral Dirhodium(II) Carboxamidates

✍ Scribed by Michael P. Doyle; Ming Yan; Iain M. Phillips; Daren J. Timmons

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 94 KB
Volume: 344
Category: Article
ISSN: 1615-4150
DOI: 10.1002/1615-4169(200201)344:1<91::aid-adsc91>3.0.co;2-s

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✦ Synopsis

N-Benzyl-2-deoxyxylonolactams are accessible by highly chemoselective, diastereoselective, and enantioselective carbon-hydrogen insertion reactions of diazoacetamides. Competing aromatic cycloaddition or b-lactam formation via carbon-hydrogen insertion into a benzylic position can be minimized by the proper selection of chiral catalyst. Conformational influences are important in product preference.

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