Back to results
US 8,263,790 B2Granted
Method for enantioselective hydrogenation of chromenes
AssigneesChildren's Hospital Medical Center, Girindus America, Inc.
InventorsKenneth David Reginald Setchell, Victor Dmitrievich Sorokin
Life of this patent
Estimating the term…
Abstract
A method for preparing an enantiomeric chromane, by asymmetrically hydrogenating a chromene compound in the presence of an Ir catalyst having a chiral ligand. The method includes the enantioselective preparation of enantiomeric equol. A preferred Ir catalyst has a chiral phosphineoxazoline ligand. Enantiomeric chromanes of high stereoselective purity can be obtained.
Claims5
A method of preparing enantioselective equol of formula I:
- wherein * indicates a chiral center,
- which comprises:
- (a) providing a protected compound of formula II:
- wherein Z is a hydroxyl protecting group:
- (b) hydrogenating said compound of formula II in the presence of a chiral phosphine-oxazoline ligand catalyst of formula IV:
- wherein R is an alkyl moiety, to form an enantiomeric equol of formula III:
- wherein * indicates a chiral center and wherein Z is a hydroxyl protecting group;
- and
- (c) deprotecting said enantiomeric equol of formula III to produce the enantiomeric equol of formula I.
6 more elements
Dependencies are inferred from the claim text.