期刊
TETRAHEDRON LETTERS
卷 51, 期 19, 页码 2567-2570出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.02.143
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资金
- Albert Einstein College of Medicine
- NSF [DBI9601607, DBI0331934]
- NIH [RR017998]
- HHMI Research Resources for Biomedical Sciences
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. (C) 2010 Elsevier Ltd. All rights reserved.
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