Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 28, Pages 8193-8197Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502976
Keywords
asymmetric synthesis; enantioselectivity; heterocycles; organocatalysis; synthetic methods
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Funding
- German Research Foundation [FR3418/1-1]
- Swiss National Science Foundation
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Oxindoles with adjacent tetrasubstituted stereocenters were obtained in high yields and stereoselectivities by organocatalyzed conjugate addition reactions of monothiomalonates (MTMs) to isatin-derived N-Cbz ketimines. The method requires only a low catalyst loading (2mol%) and proceeds under mild reaction conditions. Both enantiomers are accessible in good yields and excellent stereoselectivities by using either Takemoto's catalyst or a cinchona alkaloid derivative. The synthetic methodology allowed establishment of a straightforward route to derivatives of the gastrin/cholecystokinin-B receptor antagonist AG-041R.
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