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Oxazoline N-Oxide Mediated [3+2] Cycloadditions: Application to a Formal Synthesis of a (+)-β-Methylcarbapenem (2000)

Mauduit, Marc ; Kouklovsky, Cyrille ; Langlois, Yves

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1595-1601

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ISSN: 1434-193X

Keywords: Oxazoline N-oxide ; Cycloadditions ; Cycloadditions ; Lactams ; Thienamycin ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---[3+2] Cycloaddition between a camphor-derived oxazoline N-oxide 9 and the γ,δ-unsaturated enamino ester 11 afforded the single adduct 6. A stereoselective reduction of the enamino ester side chain allowed the control of the absolute configuration of the two additional asymmetric centres. Nitrogen protection and oxidative hydrolysis of the resulting product 13, followed by further functional group manipulations, led to the β-lactam derivative 1, a known precursor of the β-methylthienamycin derivative2a.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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