Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 12436-12442Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01466
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Funding
- Reed College Marsh Cronyn Fellowship
- Reed College
- Disruptive Chemistry Fellowship program of Merck & Co., Inc. (Kenilworth, NJ)
- National Science Foundation under the CCI Center for Selective C-H Functionalization [CHE-1700982]
- National Natural Science Foundation of China [NSFC 21702126]
- China Scholarship Council
- National Institute of General Medical Sciences [R35 GM130345A]
- Nationa Institutes of Health [S10OD024998]
- Office of Science, of the U.S. Department of Energy [DE-AC02-05CH11231]
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Methods focusing on functionalizing the periphery of azacyclic scaffolds have become increasingly popular. Experimental observations show that the regioselectivity of C-C cleavage can be altered by changing the ligand set used in the coupling chemistry.
Methods that functionalize the periphery of azacylic scaffolds have garnered increasing interest in recent years. Herein, we investigate the selectivity of a solid-state Norrish-Yang cyclization (NYC) and subsequent C-C cleavage/cross-coupling reaction of a strained cyclopropane-fused azacyclic system. Surprisingly, the NYC primarily furnished a single lactam constitutional and diastereo-isomer. The regioselectivity of the C-C cleavage of the alpha-hydroxy-beta-lactam moiety could be varied by altering the ligand set used in the coupling chemistry. Experimental and computational observations are discussed.
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