Stereoselectivity in the reduction of aliphatic .alpha.-ketols with aluminum hydride reagents

Katzenellenbogen, John A.; Bowlus, Stephen B.

doi:10.1021/jo00944a001

Cited by 55 publications

(15 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As an example, by an enzymatic two‐step reaction, vicinal 1,2‐diols can be generated. These compounds are versatile building blocks for active pharmaceutical ingredients but their chemical synthesis often suffers from low stereoselectivity, toxic reactants, or low yields . Biocatalytically, we are able to access a platform of differently substituted diols selectively by the reduction of the corresponding 2‐hydroxy ketones using a diverse toolbox of alcohol dehydrogenases .…”

Section: Introductionmentioning

confidence: 99%

“…[5,6] As an example, by an enzymatic twostep reaction, vicinal 1,2-diols can be generated.T hese compounds are versatile buildingb locks for active pharmaceutical ingredients [7] but their chemical synthesis often suffers from low stereoselectivity,t oxic reactants, or low yields. [8][9][10][11][12][13][14][15][16] Biocatalytically, we are able to access ap latform of differently substituted diols selectively by the reduction of the corresponding 2-hydroxy ketones using ad iverse toolbox of alcohol dehydrogenases. [6] The 2-hydroxy ketones can also be produced biocatalytically by the carboligation of aldehydes using another tool-box of enzymes that dependo nt hiamine diphosphate (ThDP) (Scheme1).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Modularized Biocatalysis: Immobilization of Whole Cells for Preparative Applications in Microaqueous Organic Solvents

et al. 2015

View full text Add to dashboard Cite

The use of whole‐cell biocatalysts enables catalyst application in microaqueous reaction systems, in which the liquid phase consists of high substrate loadings in organic solvents, to enable access to high concentrations of easy‐to‐purify product. One current research focus is the modularization of single reaction steps to (i) enable flexible combinations into multi‐step enzyme reactions, (ii) investigate ideal reaction conditions, and (iii) facilitate catalyst handling and recycling. Therefore, we published the easy‐to‐apply encapsulation of a lyophilized whole‐cell catalyst in a polymeric membrane recently. These catalytic “teabags” were demonstrated to enable flexible catalyst combinations for multi‐step reactions and excellent recyclability during repeated batch experiments. We now describe the applicability of these “teabags” on a larger scale by using the new SpinChem reactor and a classical stirred‐tank reactor model. As an alternative, we investigate the described alginate entrapment approach and compare the results. The carboligation reaction towards (R)‐benzoin, using lyophilized E. coli that enclose Pseudomonas fluorescens benzaldehyde lyase (EC 4.1.2.38), served as a model reaction. It was demonstrated that the catalytic “teabags” are scalable and perform equally on the investigatory 5 mL scale and the preparative 140 mL reactor scale. Tested in a more advanced application, the “teabags” were proven to be useful in a one‐pot two‐step reaction for the gram‐scale production of 1‐phenylpropane‐1,2‐diol by using the SpinChem reactor, which allowed to reach an industrially relevant product concentration (32.9 g L−1) and space–time yield (8.2 g L−1 d−1).

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Modularized Biocatalysis: Immobilization of Whole Cells for Preparative Applications in Microaqueous Organic Solvents

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Subsequent hydration gives an access to a-hydroxy methyl ketones. Due to the high regioselectivity of hydration of a 1,2-or a 1,3-difunctional compound (propargylic alcohol) only a 1,2-difunctional compound is obtained [9] (logical convergence, Scheme 22).…”

Section: 2-difunctional Compoundsmentioning

confidence: 99%

Logic of organic chemistry

2016

View full text Add to dashboard Cite

A system of logic disconnection or construction of organic molecules is given to overcome serious problems in the study of organic chemistry. Based on the logic system of polar reactions of donors and acceptors several different reactions can be created to access a required target molecule. By a following careful analysis of these proposals several transformations can be detected as the preferred ones. Moreover, by the introduction of the ''umpolung'' principle additional options are given to synthesize a required molecule. These considerations were discussed in the 1,2-, 1,3-, 1,4-, 1,5-and 1,6-difunctional series.

show abstract

“…and evaporated under reduced pressure. 2a + lb (155 mg) was obtained as white solid (lit., 11) mp 42.5-44°C) in 88. 4 …”

Section: Preparations Of Dl-erythro-23-octanediol (2a+2b) Dlthreo-2mentioning

confidence: 99%

(2S, 3R)-trans-4,trans-6-Oetadiene-2, 3-diol: Structure and Absolute Configuration of a Novel Metabolite of Sorbic Acid

Kawabata

Tahara

Mizutani

1978

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

Stereoselectivity in the reduction of aliphatic .alpha.-ketols with aluminum hydride reagents

Cited by 55 publications

References 2 publications

Modularized Biocatalysis: Immobilization of Whole Cells for Preparative Applications in Microaqueous Organic Solvents

Modularized Biocatalysis: Immobilization of Whole Cells for Preparative Applications in Microaqueous Organic Solvents

Logic of organic chemistry

(2S, 3R)-trans-4,trans-6-Oetadiene-2, 3-diol: Structure and Absolute Configuration of a Novel Metabolite of Sorbic Acid

Contact Info

Product

Resources

About