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Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst
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Section:Abstract
Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of α,β-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted α,β-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
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Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C2-Symmetric Ureas
Ying Cheng, Jing An, Liang-Qiu Lu, Lan Luo, Zheng-Yi Wang, Jia-Rong Chen, and Wen-Jing XiaoThe Journal of Organic Chemistry2011 76 (1), 281-284Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C2-Symmetric Ureas
Ying Cheng, Jing An, Liang-Qiu Lu, Lan Luo, Zheng-Yi Wang, Jia-Rong Chen, and Wen-Jing XiaoThe Journal of Organic Chemistry2011 76 (1), 281-284A novel organocatalytic asymmetric cyclopropanation of β,γ-unsaturated α-ketoesters with stabilized sulfur ylides using C2-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted ...
N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives
Gong-Qiang Li, Li-Xin Dai and Shu-Li YouOrganic Letters2009 11 (7), 1623-1625N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives
Gong-Qiang Li, Li-Xin Dai and Shu-Li YouOrganic Letters2009 11 (7), 1623-1625N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-1-formylcyclopropanes was developed. With 5 mol % of triazolium salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-1-formylcyclopropanes led to 3,4-dihydro-α-pyrones ...
Rhodium-Catalyzed Hydroformylation of Cyclopropenes
William M. Sherrill and Michael RubinJournal of the American Chemical Society2008 130 (41), 13804-13809Rhodium-Catalyzed Hydroformylation of Cyclopropenes
William M. Sherrill and Michael RubinJournal of the American Chemical Society2008 130 (41), 13804-13809The first catalytic diastereo- and enantioselective hydroformylation of cyclopropenes was demonstrated. The reaction proceeds efficiently under very mild conditions and low catalyst loadings providing high yields of cyclopropylcarboxaldehydes. This novel ...
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- Published In Issue July 20, 2007
- Received March 13, 2007
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