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

Haruo Aikawa; Yusuke Takahira; Masahiko Yamaguchi

doi:10.1039/c0cc03025b

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

Haruo Aikawa, Yusuke Takahira, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1479-1481
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	5
DOIs	https://doi.org/10.1039/c0cc03025b
Publication status	Published - 2011 Feb 7

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c0cc03025b

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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.",

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AU - Aikawa, Haruo

AU - Takahira, Yusuke

AU - Yamaguchi, Masahiko

PY - 2011/2/7

Y1 - 2011/2/7

N2 - 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.

AB - 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.

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JO - Chemical Communications

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

Abstract

ASJC Scopus subject areas

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