Issue 5, 2011
From the journal:

Chemical Communications

Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures†

Haruo Aikawa,ab   Yusuke Takahiraa  and  Masahiko Yamaguchi*ac  

* Corresponding authors

a Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 980-8578, Japan
E-mail: yama@mail.pharm.tohoku.ac.jp
Fax: +81 22 795 6811
Tel: +81 22 795 6812

b International Advanced Research and Education Organization, Tohoku University, Sendai 980-8578, Japan

c WPI Advanced Institute for Materials Research, Tohoku University, Sendai 980-8577, Japan

Abstract

Single enantiomers of 1,8-di(1-adamantyl)naphthalenes were synthesized by the [4+2]cycloaddition reaction of 6-adamantylbenzyne and 2-adamantylfuran. The enantiomers were resolved by conversion into diastereomeric ketopinic acid esters. The absolute configuration was determined by X-ray analysis. Kinetic studies by CD revealed an enantiomerization barrier of 29 kcal mol−1 for 1,8-(1-adamantyl)naphthalenes.

Graphical abstract: Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures

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Article information

DOI
https://doi.org/10.1039/C0CC03025B
Article type
Communication
Submitted
04 Aug 2010
Accepted
27 Oct 2010
First published
19 Nov 2010

Chem. Commun., 2011,47, 1479-1481

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Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures

H. Aikawa, Y. Takahira and M. Yamaguchi, Chem. Commun., 2011, 47, 1479 DOI: 10.1039/C0CC03025B

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