8-Oxo-3-oxa-1-azabicyclo[4.2.0]octanes containing a chiral cente

Details 8-Oxo-3-oxa-1-azabicyclo[4.2.0]octanes containing a chiral cente 8-Oxo-3-oxa-1-azabicyclo[4.2.0]octanes containing a chiral cente

1982-05-12

1984-04-17

Raymond, Richard

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

Organic compounds

Chalcogen in the nitrogen containing substituent

42424857, C07D49804

Patent

active

044435991

ABSTRACT:
There is provided a process for the preparation of an enantiomer of a compound of formula (I) which process comprises separation thereof from a mixture of diastereoisomers of a compound of the formula (I): ##STR1## wherein R is acetyl, .alpha.-hydroxyethyl or a protected derivative thereof, and R.sup.1 and R.sup.2 are substituted or unsubstituted hydrocarbon groups, or are joined so as to form a carbocyclic or heterocyclic ring; at least one of R.sup.1 and R.sup.2 containing a chiral center, such that the enantiomer can be separated thereby; and R.sup.3 and R.sup.4 are independently hydrogen or an organic group bonded via a carbon atom to the tetrahydro-oxazine ring, or R.sup.3 and R.sup.4 are joined so as to form together with the carbon atom to which they are attached an optionally substituted C.sub.3-7 cycloalkyl or optionally substituted heterocyclyl ring.
The enantiomer is of use in the preparation of optically active carbapenem antibiotics.

REFERENCES:
patent: 4122262 (1978-10-01), Buckley et al.
patent: 4245089 (1981-01-01), Ponsford et al.
patent: 4323567 (1982-04-01), Narisada et al.
patent: 4348320 (1982-09-01), Bouffard et al.
Bouffard et al., Journal of Organic Chemistry, vol. 45, No. 6 (1980), pp. 927-1176.
Ponsford et al., Journal of the Chemical Society, No. 19 (1979), pp. 846-847.
Ponsford et al., Journal of the Chemical Society, No. 21 (1980), pp. 1085-1086.

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