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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Bibliographic Details
Published in:Organic letters Vol. 18; no. 15; pp. 3562 - 3565
Main Authors: Cioc, Razvan C., Schuckman, Peter, Preschel, Hans D., Vlaar, Tjostil, Ruijter, Eelco, Orru, Romano V. A.
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 05.08.2016
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
CYANOHYDRINS
ACTIVATION
MECHANISM
ANALOGS
MODE
REACTIVITY
PASSERINI REACTION
ISSN:1523-7060, 1523-7052, 1523-7052
Online Access:Get more information
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b01481