The first synthesis of optically active 1-substituted taurines

Xu, Jiaxi; Xu, Shu; Zhang, Qihan

doi:10.1002/hc.20133

Cited by 17 publications

(4 citation statements)

References 27 publications

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“…In recent decades, taurine derivatives have gained increasing attention due to their biological actions and potential therapeutic applications, and have stimulated considerable interest in their asymmetric synthesis. 13,14 On the other hand, b-sultams are the sulfonyl analogs of b-lactams and are intriguing molecular entities from chemical and pharmacological viewpoints because they are approximately 10 3 -fold more reactive than b-lactams. 15,16 However, research toward the asymmetric construction of the simple architectures of these biologically relevant b-amino organosulfur compounds has been surprisingly limited.…”

Section: Resultsmentioning

confidence: 99%

Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

et al. 2012

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Chiral Ionic Broensted Acid-Achiral Broensted Base Synergistic Catalysis for Asymmetric Sulfa-Michael Addition to Nitroolefins. -The present new method is applicable to both aromatic and aliphatic nitroolefins giving the desired addition products with excellent enantioselectivities. The catalyst system consists of 2,6-lutidine and a binaphthyl catalyst with homogeneous axial chirality. Although aromatic nitroolefins (I) require only very small amounts of catalyst (1 mol%), slightly more amounts must be used for sterically demanding and aliphatic nitroolefins (2 mol%). Pentyl derivative (Va) is the key intermediate for the first asymmetric syntheses of both optically active taurine derivative (VI) as well as substituted β-sultam (VII). -(URAGUCHI, D.; KINOSHITA, N.; NAKASHIMA, D.; OOI*, T.; Chem. Sci. 3 (2012) 11, 3161-3164,

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Section: Resultsmentioning

confidence: 99%

Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

et al. 2012

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“…As part of our ongoing program to synthesize structurally diverse substituted taurines, we prepared 1‐monosubstituted and 1,1‐ and 1,2‐disubstituted taurines effectively from simple starting materials, such as alkenes, epoxides, ketones;11,15,16,18 2‐monosubstituted, and 1,2‐ and 2,2‐disubstituted taurines from various aziridines 14,19…”

Section: Resultsmentioning

confidence: 99%

Versatile Synthesis of Free and N‐Benzyloxycarbonyl‐Protected 2,2‐Disubstituted Taurines

Wang

Zhang

et al. 2007

Eur J Org Chem

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“…Several reports have already been devoted to the synthesis of taurine derivatives. 1-Substituted taurines have been synthesized from olefins, 3 from b-amino secondary alco-hols, 4 and from epoxides. 5 2-Substituted taurines have been prepared from b-amino primary alcohols, 6 from aziridines, 7 and from 2-nitroalkanesulfonic acids.…”

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Asymmetric Synthesis of 1,2-anti-Disubstituted Taurine Derivatives

Enders¹,

Iffland²,

Raabe³

2009

Synthesis

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An efficient asymmetric synthesis of anti-1,2-disubstituted taurine derivatives through nucleophilic addition of phenylmethanesulfonate to various N-acylimines in the presence of 1,2:5,6-di-O-isopropylidene-a-D-allofuranose as a chiral auxiliary is described. The taurine derivatives were obtained in three steps with good overall yields (36-61%) and excellent enantiomeric excesses (83-98%). The diastereomeric excesses of 15-91% could be improved to 90-98% by column chromatography or recrystallization. The relative and absolute configurations of the products were determined by means of an X-ray crystal structure analysis.Sulfonic acids and their derivatives are important biologically active constituents of mammals, marine algae, fish, and shellfish. 1 The best known are 2-aminoethanesulfonic acid (taurine) and related compounds such as 3-aminopropanesulfonic acid (homotaurine), 2-carbamimidamidoethanesulfonic acid (N-guanidinotaurine), cysteic acid, and 2-hydroxyethanesulfonic acid (isethionic acid) ( Figure 1). Taurine is found in relatively high concentrations in the central nervous system, brain, heart, retina, and muscles, and is involved in various physiological processes such as brain development, neurotransmission, and immunomodulation. 2In view of the important physiological effects of these naturally occurring aminosulfonic acids, which can be regarded as sulfur analogues of amino acids, the development of new diastereo-and enantioselective methods for their synthesis is highly desirable.Several reports have already been devoted to the synthesis of taurine derivatives. 1-Substituted taurines have been synthesized from olefins, 3 from b-amino secondary alcohols, 4 and from epoxides. 5 2-Substituted taurines have been prepared from b-amino primary alcohols, 6 from aziridines, 7 and from 2-nitroalkanesulfonic acids. 8 1,1-Disubstituted taurines are available from ketones through Corey-Chaykovsky epoxidation, episulfidation, and ammonia-induced ring cleavage, followed by oxidation with performic acid. 9 1,2-Disubstituted taurines have been prepared from olefins 9,10 and from epoxides. 5 2,2-Disubstituted taurines have been synthesized from aziridines, 11 from amino alcohols, 6f and from ketones through the Strecker amino acid synthesis. 12Our group has described an efficient asymmetric synthesis of 2-substituted and 1,2-disubstituted taurine derivatives through aza-Michael addition of the enantiopure hydrazines (2S)-2-(methoxymethyl)pyrrolidin-1-amine (SAMP) or (2R,3aR,6aR)-2-(methoxymethyl)hexahydrocyclopenta[b]pyrrol-1(2H)-amine (RAMBO) to a,b-unsaturated sulfonates in the presence of a Lewis acid catalyst. 13In our ongoing research on the asymmetric synthesis of sulfonic acid derivatives, we planned to gain access to 1,2-disubstituted taurine derivatives through nucleophilic addition to an N-acylimine of a chiral phenylmethanesulfonate bearing an enantiopure sugar auxiliary.In previous communications and a full paper, 14 we reported on efficient asymmetric electrophilic a-substitution reactions of various a...

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The first synthesis of optically active 1-substituted taurines

Cited by 17 publications

References 27 publications

Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

Versatile Synthesis of Free and N‐Benzyloxycarbonyl‐Protected 2,2‐Disubstituted Taurines

Asymmetric Synthesis of 1,2-anti-Disubstituted Taurine Derivatives

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