Journal
TETRAHEDRON
Volume 66, Issue 21, Pages 3655-3661Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.081
Keywords
Catalyst design; Conjugate addition; Doubly stereocontrolled; alpha-Amino acids; Carbohydrates
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Funding
- National Natural Science Foundation of China [20702044, 20962023]
- Program for New Century Excellent Talents in University
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A novel class of easily preparative, cheap, and fine-tunable bifunctional chiral tertiary amine thiourea organocatalysts have been developed by combining both acyclic diamines derived from acyclic a.-amino acids and carbohydrates. These organocatalysts promoted the enantioselective conjugate addition of acetylacetone to various nitroolefins in good yields (up to 93%) with good enantioselectivities (up to 91% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures into a single catalyst. Notably, it offers a simple and convenient doubly stereocontrolled approach for the catalytic asymmetric synthesis of a chiral organic molecule. (C) 2010 Elsevier Ltd. All rights reserved.
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