One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides

Răzvan C Cioc, Daan J H van der Niet, Elwin Janssen, Eelco Ruijter, Romano V A Orru

Research output: Contribution to JournalArticleAcademicpeer-review

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.

Original languageEnglish
Pages (from-to)7808-7813
Number of pages6
JournalChemistry: A European Journal
Volume21
Issue number21
DOIs
Publication statusPublished - 18 May 2015

Keywords

  • Albuterol/chemical synthesis
  • Aldehydes/chemical synthesis
  • Amino Alcohols/chemical synthesis
  • Bronchodilator Agents/chemical synthesis
  • Combinatorial Chemistry Techniques
  • Cyanides/chemical synthesis

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