Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts. Academic Article uri icon

Overview

abstract

  • Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets.

publication date

  • May 1, 2010

Identity

PubMed Central ID

  • PMC3140427

Scopus Document Identifier

  • 77950370982

Digital Object Identifier (DOI)

  • 10.1016/j.tetlet.2010.02.143

PubMed ID

  • 21785516

Additional Document Info

volume

  • 51

issue

  • 19