101067-95-2Relevant articles and documents
Oxazoline N-oxide mediated [3+2] cycloadditions: Application to a formal synthesis of a (+)-β-methylcarbapenem
Mauduit, Marc,Kouklovsky, Cyrille,Langlois, Yves
, p. 1595 - 1601 (2007/10/03)
[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 derivative 2a.
A FACILE, STEREOCONTROLLED ENTRY TO KEY INTERMEDIATES FOR THIENAMYCIN SYNTHESIS FROM ETHYL (S)-3-HYDROXYBUTANOATE
Chiba, Toshiyuki,Nagatsuma, Masako,Nakai, Takeshi
, p. 1343 - 1346 (2007/10/02)
A new synthetic approach to optically active key intermediates for thienamycin synthesis is described which involves the highly stereocontrolled transformation of the 2-azetidinone obtained via the condensation of ethyl (S)-3-hydroxybutanoate with the N-s