Process for the enantioselective synthesis of 2(R)-benzylsuccini

Details Process for the enantioselective synthesis of 2(R)-benzylsuccini Process for the enantioselective synthesis of 2(R)-benzylsuccini

1993-02-16

1994-06-14

Cintins, Marianne M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

556136, 560 41, 560 43, 585269, 502162, 502166, 502167, 546216, 546238, 544172, 544355, 544386, 540575, 5483341, 5483741, 548540, C07D21106, C07C23102

Patent

active

053211391

ABSTRACT:
Two processes are described for the preparation of the optically pure compounds of formula 1: ##STR1## in which R.sup.1 and R.sup.2 are e.g. alkyl, R.sup.3 and R.sup.4 are e.g. hydrogen and R.sup.5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C.dbd.C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.

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