Process for the manufacture of optically active compounds

Details Process for the manufacture of optically active compounds Process for the manufacture of optically active compounds

1983-08-22

1986-03-25

Ramsuer, Robert W.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544398, 546236, 546248, 548574, 564346, 564508, 568436, 568449, 568485, 556413, C07C 9310, C07D29508

Patent

active

045784620

ABSTRACT:
The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,
by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,
is described.
The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.

REFERENCES:
patent: 2541091 (1951-02-01), Oroshnik
patent: 4041058 (1977-08-01), Cohen et al.
European Publication No. 0 068 506 (1-1983).
Oroshnik et al., J. Am. Chem. Soc., vol. 72 (1950) pp. 4608-4613.
Ohsugi et al., Biol. Chem., vol. 38 (1974) pp. 1925-1928.
Mornet et al., C.R. A cad. Sc., Ser. C, 279 (1974) pp. 229-232.
Mornet et al., J. Organomet. Chem., vol. 86 (1975) pp. 57-67.
Mornet et al., Bull. Chem. Soc. Fr., (1977) pp. 737-741.
Mornet et al., Synthesis, (1977) pp. 786-787.
Mornet et al., Tetrahedron Lett. (1977) pp. 167-174.

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