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ChemInform Abstract: Stereocontrol in Organic Synthesis Using Silicon-Containing Compounds. A Formal Synthesis of (.+-.)-Thienamycin.

✍ Scribed by I. FLEMING; J. D. KILBURN

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199901234

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✦ Synopsis

Stereocontrol in Organic Synthesis Using Silicon-Containing Compounds. A Formal Synthesis of (±)-Thienamycin.

-The precursor (IX) of the title antibiotic is prepared from aldol product (Ib), which has a silyl group in the side chain as hydroxy surrogate. The trans disposed substituents at the azetidine ring are obtained by Mitsunobu reaction of hydroxamate (IV). In contrast, the enolate (X) reacts with silylimines (XI) to give cis-lactams (XII) as major products. -(FLEMING, I.; KILBURN,

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