The resolution of endo-bicyclo[3.3.1]non-6-en-3-carboxylic acid and its conversion to optically active adamantanones

✍ Scribed by H. Numan; C.B. Troostwijk; J.H. Wieringa; Hans Wynberg

• Book ID: 104244384
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 185 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93269-1

✦ Synopsis

We needed in the synthesis of models to study the No facile describe here, that chiral adamantanones in order to explore their usefulness as starting materials stable optically active 1,2-dioxetanes. 1 The latter compounds are suitable circular polarisation of chemiluminescence. 2 route to optically active substituted adamantanones isavailable. 3a-c We will the T-route cyclisation 4a-c,5 of certain endo-bicyclo[3-3-llnon-6-en-3-yl derivatives provides such a pathway. We wish to report the resolution of the endo-bicyclo[3.3.1]non-6-en-3-carboxylic acid (I)4a'b96 and its successful conversion to: i) ii) iii) The absolute established. (1s) 4,4-dimethyl-adamantan-2-one (VI) (see scheme 1); the (1R) (45) 4e-chloro-adamantan-2-one (VII) and (1R) (4R) 4a-chloroadamantan-e-one (VIII); (1s) 4,4-dideutero-adamantan-2-one (IX). configurations of the acid (+) I and of the ketones VI, VII, VIII and IX were Determination of the optical purities of the starting acid (t) I and the (t) (1s) 4,4-dimethyl-adamantan-Pane (VI) showed complete retention of enantiomeric excess.