Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.
Tetrahedron Lett
; 51(19): 2567-2570, 2010 May 01.
Article
em En
| MEDLINE
| ID: mdl-21785516
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Tetrahedron Lett
Ano de publicação:
2010
Tipo de documento:
Article
País de afiliação:
Estados Unidos