Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures |
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| Authors: | Aikawa Haruo Takahira Yusuke Yamaguchi Masahiko |
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| Institution: | Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 980-8578, Japan. |
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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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