Enantioselective acylation of chroman-4-ols catalysed by lipase from Pseudomonas cepecia (Amano PS)

Sathunuru, Ramadas; Krupadanam, G. L. David

doi:10.1016/s0957-4166(97)00366-2

Cited by 9 publications

(7 citation statements)

References 6 publications

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“…The conversion rate of the product was calculated by comparison of the ketone peak with the alcohol peak after HPLC analysis of the crude product. ( S )‐6‐chlorochroman‐4‐ol : white solid, isolated yield 94% (8.2 g), M.p. : 83‐85°C, [α] D 25 = −26,5 (c 1, CHCl 3 ) >99% ee; Lit.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

Şahin

2020

Chirality

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Chromane, which has a fused cyclic structure, is a significant molecule that can be found in the structure of many important compounds. Lactobacillus paracasei BD101 was demonstrated as whole‐cell biocatalyst for the synthesis of (S)‐6‐chlorochroman‐4‐ol with immense enantioselectivity. The conditions of asymmetric reduction were optimized one factor by one factor using L paracasei BD101 to achieve enantiomerically pure product and complete conversion. Using these obtained optimization conditions, asymmetric reduction of 6‐chlorochroman‐4‐one was performed under environmentally friendly conditions; 6‐chlorochroman‐4‐one, having a fused cyclic structure as previously noted to be difficult to asymmetric reduction with biocatalysts, was enantiomerically reduced to (S)‐6‐chlorochroman‐4‐ol with an enantiomeric excess >99% on a high gram scale. This study is the first example in the literature for the enantiopure synthesis of (S)‐6‐chlorochroman‐4‐ol using a biocatalyst. Also notably, the optical purity of (S)‐6‐chlorochroman‐4‐ol obtained in this study through asymmetric bioreduction using whole‐cell biocatalyst is the highest value in the literature. In this study, (S)‐6‐chlorochroman‐4‐ol was produced on a gram scale by an easy, inexpensive, and environmentally friendly method, which has shown the production of valuable chiral precursors for drug synthesis and other industrial applications. This study provides a convenient method for the production of (S)‐6‐chlorochroman‐4‐ol, which can meet the industrial green production demand of this chiral secondary alcohol.

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Section: Methodsmentioning

confidence: 99%

“…The conversion rate of the product was calculated by comparison of the ketone peak with the alcohol peak after HPLC analysis of the crude product. (S)-6-chlorochroman-4-ol 31…”

Section: Generalmentioning

confidence: 99%

Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

Şahin

2020

Chirality

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“…For spectral and physical data, see ref. 39 Compounds 5h-j; General Procedure p-TsOH•H 2 O (0.25 mol) was added to a solution of alcohol 11 (0.1 mol) in anhyd toluene (4 L), and the solution was refluxed until the complete conversion of the starting material. Then, the reaction mixture was cooled to r.t., washed with H 2 O (2 × 1 L), 10% aq NaHCO 3 (3 × 1 L), and H 2 O (2 × 1 L), dried (anhyd Na 2 SO 4 ), and evaporated under reduced pressure.…”

Section: -Bromochroman-4-ol (11j)mentioning

confidence: 99%

Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides

et al. 2018

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“…The organic layer was filtered through a plug of silica and the solvent removed under reduced pressure to leave the product which was purified by column chromatography if necessary. Characterisation data and ee determination methods for reduction products [43][44][45][46][47][48][49][50] are given in the Supporting Information.…”

Section: (S)-n-((1r2r)-12-diphenyl-2-((s)-pyrrolidine-5-carboxamidomentioning

confidence: 99%

Application of Proline‐Functionalised 1,2‐Diphenylethane‐1,2‐diamine (DPEN) in Asymmetric Transfer Hydrogenation of Ketones

Manville

Docherty²,

Padda³

et al. 2011

Eur J Org Chem

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Enantioselective acylation of chroman-4-ols catalysed by lipase from Pseudomonas cepecia (Amano PS)

Cited by 9 publications

References 6 publications

Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides

Application of Proline‐Functionalised 1,2‐Diphenylethane‐1,2‐diamine (DPEN) in Asymmetric Transfer Hydrogenation of Ketones

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