期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 19, 页码 6653-6659出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo101547w
关键词
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资金
- NSF [CHE-0910604]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0910604] Funding Source: National Science Foundation
Suzuki cross-coupling of a 1,8-dihalonaphthalene with 4-methoxy-3-methylphenylboronic acid or 4-acet-amidophenylboronic acid and subsequent functional group transformation gave 1,8-bis(3'-methyl-4'-anilino)naphthalene, 16, and 1,8-bis(4'-anilino)naphthalene, 21, in 65% and 90% overall yield, respectively. These congested compounds exhibit two cofacial aniline rings that favor a proximate, parallel arrangement of covalently attached cinnamoyl units suitable for stereoselective photodimerization. The [2 + 2]cycloaddition was found to proceed with high yield and exclusive formation of cis,trans, cis-cyclobutane-1,2-dicarboxylic acids. Amide formation with cinnamoyl chloride and template 21 followed by photochemical dimerization and acidic hydrolysis gave beta-truxinic acid, 10, in 69% overall yield. Coupling of 21 and (E)-3-(3,4-dimethylphenyl)acrylic acid in the presence of EDC, UV irradiation, and cleavage gave cis,trans,cis-3,4-bis(3,4-dimethylphenyl)cyclobutane-1,2-dicarboxylic acid, 26, in 60% yield. In both cases, the template was quantitatively recovered.
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