Merck + Co., Inc.

Other

Lyndon C Xavier

David J Mathre

Nobuyoshi Yasuda

Thomas J Blacklock

Todd K Jones

Edward J Grabowski

Ulf H Dolling

Mark A Huffman

Ann E DeCamp

Ann Decamp

Dale L Rieger

Yulan Li

Paul Sohar

Guo-Jie Ho

F Edward Roberts

Julie J Mohan

The present invention is directed to a compound represented by the structural formula: ##STR1## wherein Z-- represents a negatively charged counterion.

Boronic acid compound

The present invention is directed to a process of making 2-aryl carbapenems of formula 1 from a compound of formula A. ##STR1## wherein compound A is reacted with a silyl protected boronic acid compound of the formula B: ##STR2## and wherein Ar is selected from the group consisting of: ##STR3##

Preparation of 2-aryl carbapenems

The present invention is directed to a process of making 2-Aryl Carbapenems of Formula 1 from a compound of formula 2. ##STR1##

Preparation of 2-aryl carbapenems via a boronic acid coupling reaction

The present invention is directed to intermediates of the following formula which are useful in the preparation of Carbapenem-antibiotics ##STR1##

Boron containing intermediates useful in the preparation of carbapenems

The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl- methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of diborane, borane-dimethyl sulfide or borane-tetrahydrofuran reductions of ketones to secondary alcohols.

Chiral catalysts for reduction of ketones and process for their

Chiral boron catalysts for reduction of ketones and process for their

5,6-Dihydro-4-(R-amino)-4H-thieno[2,3-b]-thiopyran-2-sulfonamide-7,7-dioxid e is a potent carbonic anhydrase inhibitor useful in the treatment of ocular hypertension and glaucoma. The S-(+)-enantiomer of that compound, the more active enantiomer, is prepared by a process involving an intermediate step of an enantioselective reduction of a carbonyl group employing an oxazaborolidine chiral catalyst.

Enantiospecific synthesis of

The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl-methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of borane-dimethyl sulfide reductions of ketones to secondary alcohols.

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Edison, NJ, United States of America

Lyndon C Xavier