A novel efficient route for preparation of chiral β-hydroxycarboxylic acid: Asymmetric hydration of unsaturated carboxylic acids catalyzed by heterobimetallic complex wool–palladium–cobalt

Wang, Siqian; Wang, Ziwei; Yang, Lin-Chun; Dong, Jin-Long; Chi, Caiqin; Sui, Danni; Wang, Yongzhao; Ren, Jianguo; Hung, Mei-Yu; Jiang, Ying‐Yan

doi:10.1016/j.molcata.2006.08.073

Cited by 24 publications

(8 citation statements)

References 38 publications

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“…In contrast, asymmetric transformations with synthetic hydration catalysts are strongly opposed by the poor nucleophilicity and electrophilicity of water, and are often associated with harsh reaction conditions, formation of adverse side products and/or complete lack of selectivity (Resch and Hanefeld 2015). This leads to the infrequent use of acid- or base-catalysed chemical hydrations in organic synthesis (Resch and Hanefeld 2015) and to the few reports on selective hydration routes by means of chemical synthesis (Xue et al 2004; Wang et al 2007; Boersma et al 2010). Hydratases are able to cope with these inherent restraints by virtue of providing a carefully orchestrated environment for chiral (bio)synthesis, i.e.…”

Section: Introductionmentioning

confidence: 99%

On the current role of hydratases in biocatalysis

Engleder

Pichler

2018

Appl Microbiol Biotechnol

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Water addition to carbon-carbon double bonds provides access to value-added products from inexpensive organic feedstock. This interesting but relatively little-studied reaction is catalysed by hydratases in a highly regio- and enantiospecific fashion with excellent atom economy. Considering that asymmetric hydration of (non-activated) carbon-carbon double bonds is virtually impossible with current organic chemistry, enzymatic hydration reactions are highly attractive for industrial applications. Hydratases have been known for several decades but their biocatalytic potential has only been explored over the past 15 years. As a result, a considerable amount of information on this enzyme group has become available, enabling their development for practical applications. This review focuses on hydratases catalysing water addition to non-activated carbon-carbon double bonds, and examines hydratases from a biochemical, structural and mechanistic angle. Current challenges and opportunities in hydration biocatalysis are discussed, and, ultimately, their potential for organic synthesis is highlighted.

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Section: Introductionmentioning

confidence: 99%

On the current role of hydratases in biocatalysis

Engleder

Pichler

2018

Appl Microbiol Biotechnol

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“…Air was delivered at 17 psi; its flow was measured using the method described in Ref. . To ensure a constant flow, a BRP (40 psi) was applied before the air tank.…”

Section: Methodsmentioning

confidence: 99%

“…Air was delivered at 17 psi;i ts flow was measured using the method described in Ref. [20].T oe nsure ac onstant flow,aBRP (40 psi)w as applied before the air tank. An aqueous solution of 1 (1 gL À1 ,4 0mL) was pumped at 60 mLmin À1 ,j oining the airflow at the T-junction, before entering the column in which the oxidation occurs in approximately 10 min.…”

Section: Synthesis Of (R)-3-hydroxy-2-methylpropanoic Acid (2)mentioning

confidence: 99%

Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril

et al. 2017

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The chemoenzymatic flow synthesis of enantiomerically pure captopril, a widely used antihypertensive drug, is accomplished starting from simple, inexpensive, and readily available reagents. The first step is a heterogeneous biocatalyzed regio‐ and stereoselective oxidation of cheap prochiral 2‐methyl‐1,3‐propandiol, performed in flow using immobilized whole cells of Acetobacter aceti MIM 2000/28, thus avoiding the use of aggressive and environmentally harmful chemical oxidants. The isolation of the highly hydrophilic intermediate (R)‐3‐hydroxy‐2‐methylpropanoic acid is achieved in‐line by using a catch‐and‐release strategy. Then, three sequential high‐throughput chemical steps lead to the isolation of captopril in only 75 min. In‐line quenching and liquid–liquid separation enable breaks in the workflow and other manipulations to be avoided.

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“…From 1 a (0.200 g, 2.22 mmol), derivative ( R )‐(−)‐ 2 a was obtained (0.231 g, 89 %): ee =94 % (determined from the corresponding methyl ester) [ α ] D =−11.3 ( c =1.00, EtOH), ref. ; 1 H NMR (CDCl 3 , 300 MHz): δ =5.70 (1 H, bs), 3.75 (1 H, d, J= 6.0 MHz), 2.74 (1 H, m), 2.10 (1 H, s,), 1.22 ppm (3 H, d, J= 7.4 MHz); 13 C NMR (CDCl 3 , 75 MHz): 180.1, 64.0, 41.6, 13.2 ppm.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Enantiomerically Enriched 2‐Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3‐Diols Mediated by Acetobacter aceti

et al. 2016

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The stereoselective desymmetrisation of achiral 2‐alkyl‐1,3‐diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2‐hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available to organic chemists for the development of sustainable manufacturing processes.

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A novel efficient route for preparation of chiral β-hydroxycarboxylic acid: Asymmetric hydration of unsaturated carboxylic acids catalyzed by heterobimetallic complex wool–palladium–cobalt

Cited by 24 publications

References 38 publications

On the current role of hydratases in biocatalysis

On the current role of hydratases in biocatalysis

Chemoenzymatic Synthesis in Flow Reactors: A Rapid and Convenient Preparation of Captopril

Synthesis of Enantiomerically Enriched 2‐Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3‐Diols Mediated by Acetobacter aceti

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