Chiral azetidinone epoxides

Details Chiral azetidinone epoxides Chiral azetidinone epoxides

1988-03-25

1990-06-26

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D40514, C07D40504, C07D41314, C07F 965

Patent

active

049373315

ABSTRACT:
Epoxyimines, formed from epoxyaldehydes, react via cycloaddition with amino-protected glycyl halides to provide 3-protected-amino-4-(substituted oxiranyl)azetidinones represented by the formula ##STR1## wherein, e.g., R is protected amino; R.sub.1 and R.sub.2 is H, alkyl, phenyl, etc.; and R.sub.3 inter alia a nitrogen-protecting group. Chiral epoxyimines from chiral epoxyaldehydes induce high levels of asymmetric induction during the cycloaddition to provide substantially one diastereomer of the 3,4-disubstituted azetidinone. For example, the epoxyimine formed with (2R,3S)-2-formyl-3-phenyloxirane and 2,4-dimethoxybenzylamine is reacted with phthalimidoacetyl chloride to provide [3R,4R,4(2S,3S]-1-(2,4-dimethoxybenzyl)-3-phthalimido-4-(3-phenyloxiran-2- yl)-2-azetidinone.
The epoxy-substituted azetidinones are useful intermediates for .beta.-lactam antibiotic compounds.

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patent: 4699986 (1987-10-01), Hubschwerlen et al.
Gigg, Carbohydrate Research, 100, C5-9, (1982).
Fakuyama, Chem. Abs. 102, 78618(b) 1984.
"Protecting Groups in Organic Chemistry" (1981), Green, ed., p. 268.
Kyowa, Chem. Abs. 102, 113170y (1982), and index entry sheet.
S. Uyeo et al., "Synthesis of 1-Carbacephem Derivatives", Chem. Pharm. Bull., 28 (5) 1563-1577 (1980).

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