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Bottom-Up Synthesis of Optically Active Oligonaphthalenes:  Three Different Pathways for Controlling Axial Chirality1

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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan, School of Pharmaceutical Sciences, University of Shizuoka, Yada, Shizuoka, 422-8002, Japan, and Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima, 737-0112, Japan
Cite this: J. Org. Chem. 2006, 71, 17, 6579–6587
Publication Date (Web):July 26, 2006
https://doi.org/10.1021/jo060974v
Copyright © 2006 American Chemical Society
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Abstract

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The oxidative homocoupling of optically active binaphthalenes 1a−d with a stoichiometric amount of CuCl2 and amines afforded quaternaphthalenes 2a−d in up to 93% de. The high diastereoselectivities were achieved through three different pathways (epimerization of the axis together with diastereoselective crystallization, thermodynamic, and kinetic control pathways). The type of side chains on the naphthalene influenced which pathway dominates. Three pathways were applicable to octinaphthalenes (8a−d) and hexadecanaphthalene 10a with 46−99% de. The absolute configuration of the newly formed axial bond was determined by (1) X-ray crystallographic analysis, (2) transformation to known compounds 15 and 16, (3) CD spectra of oligonaphthalenes with two pyrene rings as exciton parts, and (4) the shift values in 13C NMR spectra of 13C-enriched derivatives 29−31 toward chiral shift reagent Eu(+tfc)3.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

 Kyoto University.

‡

 University of Shizuoka.

§

 Hiroshima International University.

Supporting Information Available

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CD and UV spectra of 22−25, full experimental details and characterization data of all new compounds, and crystallographic information file (CIF) of (S,S,S)-2d (CCDC 606842). This material is available free of charge via the Internet at http://pubs.acs.org.

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