The First Enantiomerically Pure Synthesis of (S)- and (R)-Naftopidil Utilizing Hydrolytic Kinetic Resolution of (±)-(α-Naphthyl) Glycidyl Ether

2004 ◽  
Vol 33 (9) ◽  
pp. 1212-1213 ◽  
Author(s):  
Kiran Kumar Kothakonda ◽  
D. Subhas Bose
Keyword(s):  
Kinetic Resolution ◽  
Glycidyl Ether ◽  
Enantiomerically Pure ◽  
Hydrolytic Kinetic Resolution

A convenient synthesis of the enantiomerically pure β-blocker (S)-betaxolol using hydrolytic kinetic resolution

2005 ◽  
Vol 16 (23) ◽  
pp. 3802-3806 ◽  
Author(s):  
Ramesh A. Joshi ◽  
Dinesh R. Garud ◽  
M. Muthukrishnan ◽  
Rohini R. Joshi ◽  
M.K. Gurjar
Keyword(s):  
Kinetic Resolution ◽  
Enantiomerically Pure ◽  
Hydrolytic Kinetic Resolution ◽  
Convenient Synthesis ◽  
Β Blocker

Chemoenzymatic synthesis of the chiral herbicide: (S)-metolachlor

2006 ◽  
Vol 84 (8) ◽  
pp. 1058-1063 ◽  
Author(s):  
Liangyu Zheng ◽  
Suoqin Zhang ◽  
Fang Wang ◽  
Gui Gao ◽  
Shugui Cao
Keyword(s):  
Chemical Method ◽  
Kinetic Resolution ◽  
Extraction Procedure ◽  
Chemoenzymatic Synthesis ◽  
Optimal Conditions ◽  
Acid Product ◽  
Enantiomerically Pure ◽  
Hydrolytic Kinetic Resolution ◽  
Simple Chemical ◽  
Simple Extraction

A chemoenzymatic approach for the production of (S)-metolachlor, one of the most widely used herbicides, has been developed. The starting material (S)-N-(2-ethyl-6-methylphenyl)alanine was obtained by the use of lipase-catalyzed hydrolytic kinetic resolution. Under the optimal conditions, the good activity and excellent enantioselectivity of lipase B from Candida antarctica (CAL-B,E > 100) are achieved in diethyl ether – water (15% v/v), which is about 9.7-fold more enantioselective than that in a pure buffered aqueous solution (E = 12.1). After a simple extraction procedure is used to separate the acid product from the remaining ester, the remaining ester is racemized, providing the basis for the continuous resolution process. Then (S)-metolachlor is synthesized by a simple chemical method using the enantiomerically pure (S)-acid.Key words: (S)-metolachlor, herbicide, CAL-B, (S)-N-(2-ethyl-6-methylphenyl)alanine, resolution.

Stereochemistry of epoxide carbonylation using bimetallic Lewis acid/metal carbonyl complexes

2004 ◽  
Vol 76 (3) ◽  
pp. 557-564 ◽  
Author(s):  
Y. D. Y. L. Getzler ◽  
Viswanath Mahadevan ◽  
E. B. Lobkovsky ◽  
G. W. Coates
Keyword(s):  
Lewis Acid ◽  
Kinetic Resolution ◽  
Metal Carbonyl ◽  
Carbonyl Complexes ◽  
Enantiomerically Pure ◽  
Metal Carbonyl Complexes ◽  
Pure Complex

The stereochemistry of epoxide carbonylation using bimetallic [Lewis acid]+[Co(CO)4]- complexes is reported. The achiral complex [(salph)Al(THF)2][Co(CO)4] stereospecifically carbonylates cis- and trans-2-butene oxide to the trans- and cis-β-lactones, respectively. Preliminary experiments regarding the carbonylative kinetic resolution of racemic trans-2-butene oxide using the enantiomerically pure complex [(R,R-salcy)Al(THF)2][Co(CO)4] are also reported.

A Versatile Co(bisalen) Unit for Homogeneous and Heterogeneous Cooperative Catalysis in the Hydrolytic Kinetic Resolution of Epoxides

2009 ◽  
Vol 15 (16) ◽  
pp. 3951-3955 ◽  
Author(s):  
Krishnan Venkatasubbaiah ◽  
Christopher S. Gill ◽  
Tait Takatani ◽  
C. David Sherrill ◽  
Christopher W. Jones
Keyword(s):  
Kinetic Resolution ◽  
Cooperative Catalysis ◽  
Hydrolytic Kinetic Resolution
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