Journal
TETRAHEDRON-ASYMMETRY
Volume 25, Issue 8, Pages 617-624Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2014.03.008
Keywords
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Funding
- National Natural Science Foundation of China [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials [K201314]
- Graduate Students Foundation of Jiangsu Normal University [2013YYB123]
- Undergraduate Students Foundation of School of Chemistry and Chemical Engineering [HXKY2013C002]
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The first catalytic asymmetric homo-1,3-dipolar cycloadditions of azomethine ylides have been established via SPINOL-derived chiral phosphoric acid-catalyzed pseudo four-component reactions of aldehydes and 2-aminomalonates, resulting in the stereoselective construction of chiral imidazolidine scaffolds with two stereogenic centers in generally high yields and with good stereoselectivities (up to 81% yield, all >20:1 dr, up to 93% ee). This protocol provides easy access to synthetically and pharmaceutically important chiral imidazolidines via the formation of one ring system, two stereogenic centers, and four new bonds in a single step. (C) 2014 Elsevier Ltd. All rights reserved.
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