期刊
TETRAHEDRON LETTERS
卷 54, 期 6, 页码 462-465出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.11.053
关键词
Asymmetric catalysis; Henry reaction; Amino alcohols; Copper; Enantioselectivity
资金
- College of Science, Engineering Agriculture
- Texas A&M University-Commerce
- National Science Foundation [CHE-1213287]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1213287] Funding Source: National Science Foundation
Two chiral pyridinylmethyl diphenylprolinolsilyl ether derivatives have been synthesized from N-alkylation of (S)-diphenylprolinolsilyl ether in a single step. They were successfully applied as ligands in the Cu(II)-catalyzed enantioselective Henry reaction between aldehydes and nitromethane in ethanol at room temperature. A variety of chiral Henry products beta-nitroalcohols were obtained in good to high yields (up to 94%) with high to excellent enantioselectivities (up to 94% ee) under the optimized reaction conditions. The results indicate that the bulky substituent diphenylprolinolsilyl ether of ligand 2 plays an important role to induce the high stereoselectivity of the process. (C) 2012 Elsevier Ltd. All rights reserved.
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