Catalytic asymmetric aminohydroxylation of olefins with carbamat

Details Catalytic asymmetric aminohydroxylation of olefins with carbamat Catalytic asymmetric aminohydroxylation of olefins with carbamat

1996-05-21

1998-06-16

Conrad, Joseph

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

Organic compounds

Carboxylic acid esters

560 29, 560115, 560160, C07C27116

Patent

active

057673047

ABSTRACT:
.beta.-Hydroxyamines and .beta.-hydroxycarbamates are synthesized from olefin substrates by means on a catalyzed asymmetric addition reaction. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhance regio- and enantio-selectivity. Carbamates are employed as an oxidant nitrogen source for the production of .beta.-hydroxysulfonamides. Excellent yields and enantiomeric efficiencies are achieved with co-solvents containing a 50/50 (v/v) mixtures of water and organic solvent. The performance of the reaction is further enhanced by omitting the addition silver or mercurial salts conventionally employed in asymmetric aminohydroxylation additions to olefins performed in neat or substantially neat solvents. .beta.-Hydroxyamines are then obtained by deprotecting the corresponding .beta.-hydroxycarbamate.

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