Optically-active diamide derivatives

Details Optically-active diamide derivatives Optically-active diamide derivatives

1982-12-09

1985-01-22

Bond, Robert T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546245, 548188, 548230, 544 54, 544 55, 544 96, 544 97, C07D 4106

Patent

active

044953550

ABSTRACT:
A novel optically active diamide derivative represented by the following general formula is provided, which is useful as a starting material for asymmetric synthesis of optically active compounds, ##STR1## wherein R.sup.1 is an acyclic or cyclic, divalent atomic group containing at least one carbon atom which will, upon substitution of one of the heterocyclic groups in the formula with a nucleophilic reagent, stand as an asymmetric center in the substitution product; R.sup.2 is a substituent which has such a configuration and a molecular size that the regioselectivity in the substitution reaction of the heterocyclic group with the nucleophilic reagent can be determined by a stereo-chemical interaction thereof with the substituent R.sup.1, the steric configuration of the two asymmetric carbon atoms to which the R.sup.2 substituents are attached being identical; X is a sulfur atom or an oxygen atom; and n is an integer which is 1 or 2. Such a diamide derivative can be prepared by subjecting the corresponding dicarboxylic acid or an anhydride thereof to a condensation reaction with the corresponding heterocyclic compound in the presence of a condensation agent. The optically-active diamide derivative can be used in the reaction with a nucleophilic reagent to obtain an optically-active compound. The resulting compound can be further modified by subjecting it to reaction with another nucleophilic reagent or to hydrolysis.

REFERENCES:
Nagao et al. "J. Am. Chem. Soc." (1982) vol. 104, pp. 2079-2081.
Webster's Third New International Dictionary of the English Language Unabridged (Merriam) p. 1130.
Chen et al. "J. Am. Chem. Soc.", vol. 103, pp. 3580-3582 (1981).
Bartlett et al. "J. Am. Chem. Soc.", vol. 102, pp. 337-342 (1980).
Hirama et al. "Tetrahedron Letters", No. 41, pp. 3937-3940 (1979).
Masamune et al. "J. Am. Chem. Soc.", vol. 103, pp. 1568-1571 (1981).
Fukuyama et al. "J. Am. Chem. Soc.", vol. 101, pp. 260-262 (1979).
Collum et al. "J. Am. Chem. Soc.", vol. 102, pp. 2118-2120 (1980).
Kocienski et al. "J. Chem. Soc., Perkin I" (1978) pp. 834-837.
Ohno et al. "J. Am. Chem. Soc.", vol. 103, pp. 2405-2406 (1981).

Affiliated with

Also associated with

Rating

Optically-active diamide derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Optically-active diamide derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically-active diamide derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-567613