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Synlett 1993; 1993(1): 59-60
DOI: 10.1055/s-1993-22348
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New Synthetic Approach to the ß-Lactams Possessing a 3-Amino Substituent via Stereodivergent Addition of the Metal Enolates of Glycine Derivatives to a Chiral Imine

Tamotsu Fujisawa* , Kouichi Higuchi, Makoto Shimizu
  • *Department of Chemistry for Materials, Mie University, Tsu, Mie 514, Japan
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Publication History

Publication Date:
19 March 2002 (online)

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Addition of the triisopropoxytitanium enolate derived from N-protected tert-butyl glycinate to a chiral imine possessing a chiral dioxolane ring gave (3R,4S)-3-amino-ß-lactam exclusively, whereas the complete reversal of the diastereofacial selectivity was observed for the chlorozinc enolate which underwent si-facial attack to give the (3S,4R)-isomer as a sole product.

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