Organocatalytic Conjugate Addition of Azide Ion to α,β‐Unsaturated Aldehydes

Abstract

An efficient and simple amine‐catatalyzed azide conjugate addition to α,β‐unsaturated aldehydes has been developed. In the presence of a catalytic amount of tertiary amine with a 1:1 mixture of NaN₃ and 37% HCl in CH₂Cl₂, α,β‐unsaturated aldehydes provided β‐azido aldehydes, which could be transformed into 1,3‐amino alcohols.

Keywords:

• 1,3‐amino alcohol
• aza‐Michael reaction
• conjugate addition
• organo‐ catalyst

Acknowledgments

This work was supported by the Ministry of Commerce, Industry and Energy (TS‐052‐03) and the Ministry of Science and Technology (KN‐0642). We thank Joel Austin, Bristol‐Myers Squibb, for making critical editorial comments about the manuscript.