- Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
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Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
- Ryoo, Jae Jeong,Yu, Jeong Jae
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- Enantioselective epoxidation by the chiral auxiliary approach: Asymmetric total synthesis of (+)-Ambrisentan
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Enantioselective and a highly concise total synthesis of Ambrisentan are described. The chiral auxiliary controlled enantioselective epoxidation (Azerad protocol), photochemical regioselective epoxide opening, and base mediated ester hydrolysis reactions
- Madhu, Madasu,Doda, Sai Reddy,Begari, Prem Kumar,Dasari, Krishna Rao,Thalari, Gangadhar,Kadari, Sudhakar,Yadav, Jhillu Singh
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p. 942 - 946
(2021/02/26)
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- Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations
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We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).
- Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong
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- Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries
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Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described.
- Leitis, Zigmārs,Lūsis, Viesturs
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p. 843 - 851
(2016/09/02)
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- N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction
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Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.
- Suzuki, Masumi,Yamazaki, Takahiro,Ohta, Hiromichi,Shima, Kyoko,Ohi, Katsuhide,Nishiyama, Shigeru,Sugai, Takeshi
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p. 189 - 192
(2007/10/03)
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- Chiral Auxiliary-Bearing Isocyanides as Synthons: Synthesis of Strongly Fluorescent (+)-5-(3,4-Dimethoxyphenyl)-4-[[N-[(4S) -2-oxo-4- (phenylmethyl) -2-oxazolidinyl] ] carbonyl] oxazole and Its Enantiomer
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Both (4S-(+)-3-(isocyanoacetyl)-4-(phenylmethyl)-2-oxazolidinone (R)-1 and its enantiomer (S)-1 have been synthesized as potentially useful synthons in asymmetric synthesis. Optically active (+)-5-(3,4-dimethoxyphenyl)-4-[[N-[(4S)-2-oxo-4-(phenylmethyl)-2
- Tang, Jian S.,Verkade, John G.
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p. 8750 - 8754
(2007/10/03)
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