Novel sulfonic acid esters and their preparation

Details Novel sulfonic acid esters and their preparation Novel sulfonic acid esters and their preparation

1986-06-02

1988-11-15

Bond, Robert T.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

558 52, 549350, 549362, 549366, 549440, 549447, C07C14368, C07C 99100, C07D22316, C07D 3155, C07D 3136, C07D 31335, C07D 31255, C07B 5300

Patent

active

047850892

ABSTRACT:
The invention relates to novel sulfonic acid esters of formula I ##STR1## wherein R.sup.1 is C.sub.5 -C.sub.6 cycloalkyl which is unsubstituted or substituted by C.sub.1 -C.sub.7 alkyl, unsubstituted or substituted phenyl, R.sup.2 is C.sub.1 -C.sub.7 alkyl, R.sup.3 is phenyl which is substituted by halogen or nitro, and the asterisk denotes a carbon atom that is either present in the preponderant number of molecules in the S configuration or in the preponderant number of molecules in the R configuration.
These compounds can be prepared by enantio-selective reduction of 4--R.sup.1 --substituted .alpha.-oxobutyric acid compounds and subsequent conversion of the resultant .alpha.-hydroxy group into the --OSO.sub.2 --R.sup.3 group. The compounds of formula I are suitable intermediates for the preparation of ACE inhibitors or precursors thereof.

REFERENCES:
patent: 4329487 (1982-05-01), Yoshio et al.
patent: 4473575 (1984-09-01), Watthey
Effenberger, Angew. Chem. 95: p. 50 [1983].
Urbach and Henning, Tetrahedron Letters 25: pp. 1143-1146 [1983].

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