title: Brønsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide.
abstract: 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.
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Răzvan C
authors.initials: RC
authors.lastname: Cioc
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Peter
authors.initials: P
authors.lastname: Schuckman
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Hans D
authors.initials: HD
authors.lastname: Preschel
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Tjøstil
authors.initials: T
authors.lastname: Vlaar
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam , De Boelelaan 1108, 1081 HZ Amsterdam, the Netherlands.
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru