Journal
ORGANIC LETTERS
Volume 19, Issue 9, Pages 2386-2389Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00913
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Funding
- Rutgers University
- NSF-MRI grant [CHE-1229030]
- SEED Grant (Rutgers University)
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A rare example of highly selective sigma N-C bond difunctionalization in bridged twisted lactams through N-C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (sew-and-cut) to access functionalized isoquinoline ring systems directly with high atom economy. C-H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in-this unusual sigma N-C amide difunctionalization are described.
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