Bronsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide
Cyanohydrins are versatile intermediates toward valuable organic compounds like alpha-hydroxy carboxylic acids, alpha-amino aids, and beta-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sour...
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| Vydáno v: | Organic letters Ročník 18; číslo 15; s. 3562 - 3565 |
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| Médium: | Journal Article |
| Jazyk: | angličtina |
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WASHINGTON
Amer Chemical Soc
05.08.2016
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| ISSN: | 1523-7060, 1523-7052, 1523-7052 |
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| Abstract | Cyanohydrins are versatile intermediates toward valuable organic compounds like alpha-hydroxy carboxylic acids, alpha-amino aids, and beta-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sources. A novel cyanide-free synthesis of O-trityl protected cyanohydrins via a catalytic Passerini-type reaction involving aldehydes and trityl isocyanide is reported. The feasibility of a catalytic asymmetric reaction is demonstrated using chiral phosphoric acid catalysis. |
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| AbstractList | Cyanohydrins are versatile intermediates toward valuable organic compounds like alpha-hydroxy carboxylic acids, alpha-amino aids, and beta-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sources. A novel cyanide-free synthesis of O-trityl protected cyanohydrins via a catalytic Passerini-type reaction involving aldehydes and trityl isocyanide is reported. The feasibility of a catalytic asymmetric reaction is demonstrated using chiral phosphoric acid catalysis. Cyanohydrins are versatile intermediates toward valuable organic compounds like α-hydroxy carboxylic acids, α-amino acids, and β-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sources. A novel cyanide-free synthesis of O-trityl protected cyanohydrins via a catalytic Passerini-type reaction involving aldehydes and trityl isocyanide is reported. The feasibility of a catalytic asymmetric reaction is demonstrated using chiral phosphoric acid catalysis. Cyanohydrins are versatile intermediates toward valuable organic compounds like α-hydroxy carboxylic acids, α-amino acids, and β-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sources. A novel cyanide-free synthesis of O-trityl protected cyanohydrins via a catalytic Passerini-type reaction involving aldehydes and trityl isocyanide is reported. The feasibility of a catalytic asymmetric reaction is demonstrated using chiral phosphoric acid catalysis.Cyanohydrins are versatile intermediates toward valuable organic compounds like α-hydroxy carboxylic acids, α-amino acids, and β-amino alcohols. Numerous protocols are available for synthesis of (O-protected) cyanohydrins, but all procedures invariably rely on the use of toxic cyanide sources. A novel cyanide-free synthesis of O-trityl protected cyanohydrins via a catalytic Passerini-type reaction involving aldehydes and trityl isocyanide is reported. The feasibility of a catalytic asymmetric reaction is demonstrated using chiral phosphoric acid catalysis. |
| Author | Schuckman, Peter Vlaar, Tjostil Cioc, Razvan C. Orru, Romano V. A. Ruijter, Eelco Preschel, Hans D. |
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| Cites_doi | 10.1002/cctc.201500225 10.1002/anie.201303572 10.1021/jacs.5b11085 10.1021/acscatal.5b02184 10.1021/jo4019528 10.1021/cr5001496 10.1002/chem.201600285 10.1039/c3cs35491a 10.1039/c4md00411f 10.1021/acs.joc.5b01173 10.1002/adsc.201400939 10.1002/cctc.201200709 10.1021/ja0639315 10.1002/adsc.201400609 10.1021/ol1007789 10.1039/c1cs15087a 10.1021/acs.jmedchem.5b01013 10.1002/chem.201303890 10.1002/chem.201302389 10.1021/jo500369y 10.1002/anie.201005336 10.1021/acs.joc.5b00594 10.1021/acs.orglett.5b03093 10.1021/jacs.5b09117 |
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| Keywords | REARRANGEMENT CYANOHYDRINS ACTIVATION MECHANISM ANALOGS MODE REACTIVITY PASSERINI REACTION |
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| Title | Bronsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide |
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