Preparation of optically active carboxylic acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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546261, 546301, 546302, 562466, 562471, 562472, 562493, C07D21355, C07D40106, C07C 5984, C07C 5986

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046910204

ABSTRACT:
Optically active carboxylic acids ##STR1## where R.sup.1 is an organic radical which is linked to the asymmetric C' atom via a carbon atom and R.sup.2 is one of the radicals R.sup.1 (but not the same radical), halogen or an organic radical which is bonded to the asymmetric C' atom via an oxygen atom, are prepared by reacting a ketene II ##STR2## with an alcohol in a homogeneous liquid phase in the presence of a tertiary amine III and then converting the resulting ester into the acid, using an optically active alcohol IV.

REFERENCES:
March, Advanced Organic Chemistry, Second Edition, pp. 106-111, 349-351, 936, 937 & 944, McGraw-Hill Pub.
Pracejus, Liebigs Annalen der Chemie, vol. 634, pp. 9-29, (1960).
Von Ernst Anders et al., Angewandte Chemie, vol. 85, pp. 16-20, (1973).
PAS Smith, The Chem. of Open-Chain Organic Nitrogen Compounds, vol. I, pp. 152, 153 and 211-213, Benjamin Pub. 1965.
P.A.S. Smith, The Chem. of Open-Chain Organic Nitrogen Compounds, vol. 2, p. 405, Benjamin Pub. 1965.
Liebigs Annalen der Chemie, vol. 634 (1960), pp. 9-29.
Angewandte Chemie, vol. 85 (1973), pp. 16-20.

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