Journal
TETRAHEDRON LETTERS
Volume 54, Issue 19, Pages 2311-2314Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.030
Keywords
Organocatalyst; Spiroindole; Michael reaction; Aldol reaction; Asymmetric catalysis
Categories
Funding
- National Institutes of Health
- Purdue University
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Organocatalytic reactions of 3-olefinic oxindoles and pentane-1,5-dial were investigated to provide access to substituted spirocyclohexane oxindoles via Michael/aldol cascade reactions. Of particular interest, we have examined the stereochemical outcome of electron withdrawing and electron-donating groups on the oxindole ring nitrogen. Interestingly, we have observed that the N-protecting group on the oxindole has critical effect on aldol ring closure leading to ultimate stereochemical outcome of the hydroxyl center. The overall process is quite efficient and afforded products with multiple stereocenters in high yields and excellent enantioselectivities (>99% ee). (C) 2013 Elsevier Ltd. All rights reserved.
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