CIS-dihydroxycyclohexadienes and their preparation
OwnerDerek R. Boyd, Howard Daltoninventors
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Abstract
This application relates to 3-substituted and 4-substituted cis-diols. Specifically, there are provided 3-substituted diols of formula (II) and 4-substituted cis-diols having (1S, 2R) and (1R, 2S) absolute configurations of formulae (III) and (IV). Also provided are processes For making such 3- and 4-substituted cis-diols using a reductive fission reaction. The compounds described herein are useful as synthons for the preparation of various compounds including therapeutics, agricultural, polymers and other classes of compounds. In formulae (II, III and IV), R is halogen, CN, aryl alkyl, alkenyl alkynyl O-alkyl, CF.sub.3 or NO.sub.2.
Claims7
A enantiomerically pure 3-substituted cis-diol having the formula:
- ##STR15## wherein R is halogen except F, CN, aryl, alkyl, alkenyl, alkyryl, O-alkyl, CF.sub.3 or NO.sub.2.
A 4-substituted cis-diol having (1S,2R) absolute configuration represented by the formula:
- ##STR16## wherein R is halogen, CN, alkyl, alkenyl, alkynyl, O-alkyl, CF.sub.3 or NO.sub.2.
A 4-substituted cis-diol having a (1R, 2S) absolute configuration represented by the formula:
- ##STR17## wherein R is halogen, CN, alkyl, alkenyl, alkynyl, O-alkyl, CF.sub.3 or NO.sub.2.
A process for pre-paring the compounds of any one of the preceding claims, the process comprising starting with a disubstituted cyclic diene diol of the formula:
- ##STR18## wherein R.sub.1 and R.sub.2 are each independently defined as halogen, CN, alkyl, alkenyl, alkynyl, aryl, O-alkyl, O-alkenyl, CF.sub.3, SR.sub.3, SOR.sub.4, SO2R.sub.5, SSR.sub.6, SNHR.sub.7, SCR.sub.3 SR.sub.9 ;
- wherein R.sub.3 -R.sub.9 are H, aryl, alkyl, alkenyl, or alkynyl;
- provided that R.sub.1 and R.sub.2 are always different;
- and subjecting the disubstituted cyclic diene diol of Formula V to a reductive fission reaction to selectively cleave R.sub.1.
Dependencies are inferred from the claim text.