Journal
TETRAHEDRON
Volume 67, Issue 6, Pages 1171-1177Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.093
Keywords
Michael addition; Nitroolefins; Camphor; Linker; Organocatalysis
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Funding
- National Science Council of the Republic of China [NSC 99-2113-M-003-002-MY3, NSC 99-2119-M-003-001-MY2]
- National Taiwan Normal University [99T3030-5, 99-D]
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A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with beta-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions. (C) 2010 Elsevier Ltd. All rights reserved.
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