New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-β-lactam

Tetrahedron Asymmetry

Volumn 10, Issue 14, 1999, Pages 2765-2773

  Barbaro, Gaetano ^a   Battaglia, Arturo ^a   Di Giuseppe, Fabio ^a   Giorgianni, Patrizia ^a   Guerrini, Andrea ^a   Bertucci, Carlo ^b   Geremia, Silvano ^c  

^a CNR   (Italy)

^b UNIVERSITY OF PISA   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALDEHYDE DERIVATIVE; BETA LACTAM DERIVATIVE; IMINE; LACTIC ACID; LITHIUM DERIVATIVE; TAXOID;

ARTICLE; CHIRALITY; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033575373     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00288-8     Document Type: Article

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43. Trace amounts (<5%) of a mixture of (3R,4s)- and (3R,4R)-3-hydroxy-3-trimethylsilyl-hydroxy-4-phenyl-β-lactams were also formed.
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47. For a detailed description of these side products see: (a) Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40, 1313-1324; (b) see Ref. 12c.
48. It is worth noting that the O-TMS protected β-lactam 15 can be easily transformed into the corresponding N-t-Boc-protected 2-methyl-phenylisoserine methyl ester via acylation at the nitrogen atom with di-tert-butyl dicarbonate followed by methanolysis. See Ref. 11.