Home
Resources
Publications
Stereocontrolled Photodimerization With Congested 1,8-bis(4'-anilino)naphthalene Templates

Stereocontrolled Photodimerization With Congested 1,8-bis(4'-anilino)naphthalene Templates

Marwan W Ghosn, Christian Wolf

J Org Chem. 2010 Oct 1;75(19):6653-9.

PMID: 20809657

Abstract:

Suzuki cross-coupling of a 1,8-dihalonaphthalene with 4-methoxy-3-methylphenylboronic acid or 4-acetamidophenylboronic 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 β-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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP101251096	4-Acetamidophenylboronic acid		101251-09-6	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: