Journal
TETRAHEDRON LETTERS
Volume 52, Issue 46, Pages 6118-6121Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.09.020
Keywords
Tetrasubstituted carbon; Hydroxymethylation; alpha-Substituted nitroacetates
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Funding
- National Natural Science Foundation of China [20902025]
- Shanghai Pujiang Program [10PJ1403100]
- East China Normal University [11043]
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Only 1 mol % of K3PO4 is efficient enough to catalyze the hydroxymethylation of alpha-substituted nitroacetates in good to excellent yield. Both aliphatic and aryl substituted nitroacetates work well under this reaction. The first catalytic asymmetric version of this reaction also reported that 10 mol % of cupreidine could catalyze this reaction up to 71% ee and 89% yield. Paraformaldehyde and formalin could both serve as the hydroxymethylation C1 unit. The synthetic application of products is also demonstrated. (C) 2011 Elsevier Ltd. All rights reserved.
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