Journal
ACS CATALYSIS
Volume 7, Issue 1, Pages 150-153Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03217
Keywords
C-H functionalization; Rh(III) catalysis; nitroalkene; enantioselective catalysis; dihydroisoquinolone
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Funding
- NIH [GM069559]
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The transition-metal-catalyzed C-H bond addition to nitroalkenes has been developed. Very broad nitroalkene scope was observed for this Rh(III)-catalyzed method, including for aliphatic, aromatic, and beta,beta-disubstituted derivatives. Additionally, various directing groups and both aromatic and alkenyl C-H bonds were effective in this transformation. Representative nitroalkane products were converted to dihydroisoquinolones and dihydropyridones in a single step and in high yield by ironmediated reduction and in situ cyclization. Moreover, preliminary success in enantioselective Rh(III)-catalyzed C-H bond addition to nitroalkenes was achieved as was X-ray structural characterization of a nitronate intermediate.
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