Journal
ORGANIC LETTERS
Volume 16, Issue 24, Pages 6420-6423Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503243a
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- University of Toronto
- Alphora, Inc.
- Canada Council
- NSERC
- CFI [19119]
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A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)(2) as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with up to >95:5 dr and with full preseveration of enantioenrichment. By circumventing a difficult nucleophilic cyanation of a hindered neopentyl iodide, this approach represents an improvement to the previously reported formal synthesis of (+)-corynoline.
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