Highly regioselective nucleophilic substitution of cyclic carbonates of threo-2,3-dihydroxy esters: synthesis of optically pure β-hydroxy esters

1994 ◽  
pp. 3513-3514 ◽  
Author(s):  
Suk-Ku Kang ◽  
Dong-Chul Park ◽  
Ho-Sik Rho ◽  
Seung-Hyun Yoon ◽  
Joon-Seob Shin
Keyword(s):  
Nucleophilic Substitution ◽  
Cyclic Carbonates ◽  
Hydroxy Esters ◽  
Optically Pure

One-pot synthesis of optically pure β-hydroxy sulfones via a heterogeneous ruthenium/diamine-promoted nucleophilic substitution-asymmetric transfer hydrogenation tandem process

2017 ◽  
Vol 7 (19) ◽  
pp. 4444-4450 ◽  
Author(s):  
Jinyu Wang ◽  
Liang Wu ◽  
Xiaoying Hu ◽  
Rui Liu ◽  
Ronghua Jin ◽  
...  
Keyword(s):  
Mesoporous Silica ◽  
Nucleophilic Substitution ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
One Pot ◽  
One Pot Synthesis ◽  
Functionalized Mesoporous Silica ◽  
Tandem Process ◽  
The One ◽  
Optically Pure

Chiral ruthenium/diamine-functionalized mesoporous silica is synthesized and its application in the one-pot synthesis of chiral β-hydroxy sulfones is investigated.

Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivatives

1976 ◽  
Vol 29 (11) ◽  
pp. 2459 ◽  
Author(s):  
BS Deol ◽  
DD Ridley ◽  
GW Simpson
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Ethyl Pyruvate ◽  
Optically Active ◽  
Phenyl Acetate ◽  
Keto Esters ◽  
Hydroxy Carboxylic Acid ◽  
Hydroxy Esters ◽  
Optically Pure

α- and β-Keto esters and amides are readily reduced by an actively fermenting mutant of Saccharomyces cerevisiae and produce optically active α- and β-hydroxy esters and amides in moderate yields. Typically, methyl 2-oxo-2-phenylacetate gave methyl (R)-(-)-2-hydroxy- 2-phenyl- acetate; 2-oxo-2-phenylacetamide gave (R)-(-)-2-hydroxy-2- phenylacetamide; ethyl benzoylacetate gave ethyl (S)-(-)-3-hydroxy-3- phenylpropionate, and ethyl 2-oxocyclohexanecarboxylate gave ethyl (1R,2S)-(+)-2-hydroxycyclohexanecarboxylate. In each case, the product obtained was optically pure. However, the reduction of ethyl pyruvate to ethyl lactate produced partially racemized products.

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