Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 10, Pages 4784-4792Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300569c
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Funding
- Defense Threat Reduction Agency (DOD-DTRA) [HDTRA1-09-1-0009]
- National Institute of General Medical Sciences, National Institute of Health [GM36700]
- National Science Foundation [TG-CHE100059]
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Derivatives of 4-hydroxyproline with a series of hydrophobic groups in well-defined orientations have been tested as catalysts for the aldol reactions. All of the modified proline catalysts carry out the intermolecular aldol reaction in water and provide high diastereoselectivity and enantioselectivity. Modified prolines with aromatic groups syn to the carboxylic acid are better catalysts than those with small hydrophobic groups (1a is 43.5 times faster than 1f). Quantum mechanical calculations provide transition structures, TS-1a(water) and TS-1f(water), that support the hypothesis that a stabilizing hydrophobic interaction occurs with 1a.
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