title: Synthesis of 1,8-di(1-adamantyl)naphthalenes as single enantiomers stable at ambient temperatures.
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.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai 980-8578, Japan.
authors.forename: Haruo
authors.initials: H
authors.lastname: Aikawa
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Takahira
authors.forename: Masahiko
authors.initials: M
authors.lastname: Yamaguchi
mesh_terms: D000218:Adamantane / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D009281:Naphthalenes; D000218:Adamantane