Chiral sugar complexes

Details Chiral sugar complexes Chiral sugar complexes

1980-07-08

1982-09-21

Ford, John M.

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

Organic compounds

Carbohydrates or derivatives

536 4, 536121, 536 53, 536 54, 536 55, C07H 1512, C07H 1702, C07H 1704, C07H 2300

Patent

active

043508111

ABSTRACT:
Chiral Schiff bases according to the general formula: ##STR1## and chiral transition metal complexes thereof, wherein at least the carbon atom of the monosaccharide to which the iminyl nitrogen atom is attached is asymmetric, and at least one of the carbon atoms adjacent the aforesaid carbon atom bears a hydroxyl group, R.sup.1 and R.sup.6 which may be the same or different, are hydrogen or lower alkyl, R.sup.2 is hydrogen, or lower alkyl or together with R.sup.10 forms a divalent hydrocarbon group, R.sup.3 is hydrogen, a sugar residue, or --CH.sub.2 OR.sup.10 in which R.sup.10 is hydrogen, lower alkyl or together with R.sup.2 forms a divalent hydrocarbon group, R.sup.4 is hydrogen or --CH.sub.2 OR.sup.10 in which R.sup.10 is hydrogen, or a lower alkyl, R.sup.5 is hydrogen, OR.sup.1 or a sugar residue, provided that both R.sup.4 and R.sup.5 are not hydrogen, R.sup.7 and R.sup.8 which may be the same or different, are hydrogen, or lower alkyl, or where p is 1, may with the cyclic ring to which CR.sup.7 R.sup.8 is attached form a fused system, R.sup.9 is hydrogen, alkyl, aralkyl, aryl or alkaryl, J is a chain of 3 or 4 atoms which with the group C A forms an aromatic system, which atoms may be carbon atoms or may be a mixture of carbon and one or more hetero atoms which may be the same or different, A is nitrogen, or ##STR2## or --NH--, L each of which may be the same or different, represents a substituent attached to a carbon atom in the chain J and is hydrogen, an alkyl group, aralkyl group, aryl, alkaryl or a substituent containing a hetero-atom; or two L's together with cyclic group to which they are attached form a fused system, m is 0 or 1, n is 0, 1 or 2, provided that n plus m is 0, 1, 2 or 3, p is 0, 1 or 2 and q is the number of carbon atoms in the chain J. The transistion metal is for example copper (II), chromium (II), manganese (II), iron (II), cobalt (II), nickel (II) or palladium (II). The aforesaid complexes may be used as catalysts in the cyclopropanation of olefins by diazoacetates to form insecticide or insecticide precursors.

REFERENCES:
patent: 3868401 (1975-02-01), Aratani
patent: 4029683 (1977-06-01), Aratani
patent: 4029690 (1977-06-01), Aratani
patent: 4225592 (1980-09-01), La Katos et al.
Aratani, Shokubai (Catalyst), vol. 19, pp. 327-333 (1977).
Adam et al., J. Chem. Soc. Chem. Comm. (1979), 234.
Hirai et al., Agric. Biol. Chem., (1976), vol. 40, 169.
Aratani et al., Tetrahedron Letter, (1975), 1707.
Aratani et al., Tetrahedron Letter, (1977), 2599.
Orioli et al., J. Amer. Chem. Soc., (1966), vol. 88, 277.
MacDonald et al., Inorganica Chimica Acta, (1979), vol. 33, L183.
Nakamura et al., J. Amer. Chem. Soc., (1978), 100, 3443, 6544.
Sacconi et al., J. Chem. Soc., (1964), 276.
Nozaki et al., Tetrahedron, (1968), 24, 3655.
Zassinovich et al., J. Organometallic Chem., (1977), 133, 377.
Robinson et al., Inorg. Chem., (1963), 2, 1178.
Hubert et al., Synthesis, (1976), 9, 600.

Affiliated with

Also associated with

Rating

Chiral sugar complexes does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Chiral sugar complexes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chiral sugar complexes will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2077042