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

被引：32

作者：

Aikawa, Haruo ^{[1
,2
]}

Takahira, Yusuke ^{[1
]}

Yamaguchi, Masahiko ^{[1
,3
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Int Adv Res & Educ Org, Sendai, Miyagi 9808578, Japan

[3] Tohoku Univ, WPI Adv Inst Mat Res, Sendai, Miyagi 9808577, Japan

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 05期

关键词：

PERI-SUBSTITUTED NAPHTHALENES; TERT-BUTYL GROUPS; HELICAL PHENANTHRENES; MOLECULAR-MECHANICS; FORCE-FIELD; DYNAMIC NMR; DERIVATIVES; CONFORMATIONS; SPECTROSCOPY; RESOLUTION;

D O I：

10.1039/c0cc03025b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Single enantiomers of 1,8-di(1-adamantyl)naphthalenes were synthesized by the [4+2]cycloaddition reaction of 6-adamantyl-benzyne 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.

引用

页码：1479 / 1481

页数：3

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