title: One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides.
abstract: A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.
authors: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands).
authors: Răzvan C
authors: RC
authors: Cioc
authors: Daan J H
authors: DJ
authors: van der Niet
authors: Elwin
authors: E
authors: Janssen
authors: Eelco
authors: E
authors: Ruijter
authors: Romano V A
authors: RV
authors: Orru
mesh_terms: D000420:Albuterol / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001993:Bronchodilator Agents / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D001993:Bronchodilator Agents; D003486:Cyanides; D000420:Albuterol
keywords: Lewis bases; aldehydes; amino alcohols; isocyanide; salbutamol