The synthesis of optically active derivatives of erythritol

Pottie, M.; Eycken, Johan Van der; Vandewalle, M.; Röper, H.

doi:10.1016/s0957-4166(00)82110-2

Cited by 28 publications

(2 citation statements)

References 14 publications

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“…m/z (ESI+) 374.1148 (M + H + ). (15), 157 (6.0), 155 (6.2), 151 (5.5), 150 (6.2), 159 (5.3), 145 (7.6), 139 (7.3), 137 (7.9), 135 (10), 131 (6.1), 117 (7.8), 116 (27), 115 (19), 102 (26), 99 (13), 98 (19), 91 (5.4), 89 (19), 88 (6.5), 86 (6.6), 85 (13), 77 (14), 76 (17), 75 (100), 74 (10), 73 (71), 71 (7.2), 70 (21), 65 (5.6), 63 (6.3), 61 (9.1), 60 (5.7), 59 (39), 58 (80), 57 (15), 56 (11), 55 (6.6), 47 (9.3), 45 (15), 44 (5.1), 43 (16), 42 (7.3), 41 (42), 39 (11). m/z (ESI+) 424.0925 (M + Na + ).…”

Section: (R)-or (S)-1-amino-3-(tert-butyl)dimethylsilyloxy-2-((3bromo...mentioning

confidence: 99%

“…Only the signals of major rotamer are reported): 1.13 (3 H, t, J 7.5, CH 3 CH 2 ), 1.33 (3 H, s, (CH 3 ) 2 C), 1.42 (3 H, s, (CH 3 ) 2 C), 2.26 (1 H, dq, J d 15.9, J q 7.5, CHHCH 3 ), 2.40 (1 H, dq, J d 15.9, J q 7.5, CHHCH 3 ), 3.62 (1 H, dd, J 4.8, 12.0, H-6), 3.76 (1 H, d, J 12.0, H-6), 4.30-4.48 (2 H, m, CH 2 Ph), 4.82 (1 H, s, H-4), 4.89 (1 H, t, J 5.1, H-6a), 5.13 (1 H, d, J 5.7, H-3a), 7.15 ( O). GC-MS: R t : 9.80 min; m/z (EI): 332 (M + , 8.2), 274, (9.7), 199 (6.2), 198 (9.5), 142 (100), 124 (6.5), 106 (8.2), 91 (26), 85 (5.8), 84 (11), 68 (16), 57 (22), 43 (6.3). m/z (ESI+) 355.1645 (M + Na + ).…”

Section: (3ar4s6as)-n-benzyl-22-dimethyl-5-propionyltetrahydro-3ah-[1...mentioning

confidence: 99%

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Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

et al. 2012

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A highly diastereoselective Ugi reaction involving a chiral cyclic imine, two enantiomerically pure isocyanides and various carboxylic acids was employed for the synthesis of polyfunctionalized pyrrolidines. Both chiral substrates have been efficiently prepared by chemoenzymatic methodologies from readily available achiral substrates. This highly convergent approach can find an application in the fragment-based drug discovery process.

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Section: (R)-or (S)-1-amino-3-(tert-butyl)dimethylsilyloxy-2-((3bromo...mentioning

confidence: 99%

Section: (3ar4s6as)-n-benzyl-22-dimethyl-5-propionyltetrahydro-3ah-[1...mentioning

confidence: 99%

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

et al. 2012

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Enzymes In Organic Synthesis

Zaks¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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This article describes applications of enzymes as catalysts in organic synthesis. It outlines the general mechanistic principles that govern enzyme‐catalyzed asymmetric synthesis and enantioselective resolutions and offers a special emphasis to the widely practiced hydrolytic reaction for the synthesis of monoesters of dicarboxylic acids and monoacylated diols. The use of hydrolytic enzymes for acylations in nonaqueous media is illustrated by the synthesis of chiral lactones and polyesters and regioselective acylations of polyhydroxy compounds. Utilization of hydrolases is also extended to resolution of racemic amines and amino acids, and enzymatic hydrolysis of nitriles. Thermodynamic and kinetic aspects of enzymatic peptide synthesis are analyzed and the most recent trends in enzyme‐catalyzed peptide condensations are illustrated by a number of examples. The synthetic utility of lyases is demonstrated by a number of aldolase‐ and ketolase‐catalyzed condensations of carbon‐carbon bonds and by the synthesis of cyanohydrins by oxynitrilases. Oxidoreductases are represented by dehydrogenases commonly used for the synthesis of chiral alcohols, lactones, hydroxy, and amino acids; by cyclohexanone monooxygenase, the enzyme that catalyzes Baeyer‐Villiger oxidation of ketones; and by lipoxygenase, which incorporates dioxygen into polyunsaturated fatty acids.

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Biotransformations with Lipases

Kazlauskas¹,

Bornscheuer²

1998

Biotechnology

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The synthesis of optically active derivatives of erythritol

Cited by 28 publications

References 14 publications

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction

Enzymes In Organic Synthesis

Biotransformations with Lipases

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