Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.
In: Tetrahedron letters, Jg. 51 (2010-05-01), Heft 19, S. 2567
Online
academicJournal
Zugriff:
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.
Titel: |
Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.
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Autor/in / Beteiligte Person: | Das, BC ; Mohapatra, S ; Campbell, PD ; Nayak, S ; Mahalingam, SM ; Evans, T |
Link: | |
Zeitschrift: | Tetrahedron letters, Jg. 51 (2010-05-01), Heft 19, S. 2567 |
Veröffentlichung: | Oxford : Elsevier ; <i>Original Publication</i>: Oxford, New York, Pergamon Press., 2010 |
Medientyp: | academicJournal |
ISSN: | 0040-4039 (print) |
DOI: | 10.1016/j.tetlet.2010.02.143 |
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