Journal
ORGANIC LETTERS
Volume 21, Issue 16, Pages 6494-6498Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02367
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Funding
- NSFC [21602087, 21871112]
- NSF of Jiangsu Province [BK20160212]
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A new double annulation cascade involving a [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) process was first reported, leading to the generation of unprecedented dibenzoannulated naphtho[2,1-b]oxecines with good to excellent yields and high stereoselectivity through catalytic scission/recombination of C-C double bonds under the mild conditions. An Y(OTf)(3)-catalyzed three-component reaction of alpha-alkynyl naphthalen-2-ols with beta,gamma-unsaturated alpha-ketoesters enabled direct ring expansion of the naphthalene ring and carbon-carbon double bond cleavage/rearrangement of alpha-ketoesters to give macrocyclic architectures.
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