REARRANGEMENT APPROACHES TO CYCLIC SKELETONS .12. ACID-CATALYZED ISOMERIZATION OF BICYCLO[3.2.1]OCT-6-EN-2-ONES INTO BICYCLO[3.2.1]OCT-3-EN-2-ONES WITHOUT RACEMIZATION

Authors
UYEHARA T INAYAMA T KOBARI T KIMURA Y YONETA N
Citation
T. Uyehara et al., REARRANGEMENT APPROACHES TO CYCLIC SKELETONS .12. ACID-CATALYZED ISOMERIZATION OF BICYCLO[3.2.1]OCT-6-EN-2-ONES INTO BICYCLO[3.2.1]OCT-3-EN-2-ONES WITHOUT RACEMIZATION, Bulletin of the Chemical Society of Japan, 70(8), 1997, pp. 1919-1921
Citations number
5
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
70
Issue
8
Year of publication
1997
Pages
1919 - 1921
Database
ISI
SICI code
0009-2673(1997)70:8<1919:RATCS.>2.0.ZU;2-T
Abstract
The treatment of a bicyclo[3.2.1]oct-6-en-2-one (3) with Amberlyst(R) (H-15) in boiling benzene gave a mixture of bicyclo[3.2.1]oct-3-en-2-o ne (5) and bicyclo[2.2.2]oct-5-en-2-one (6). The ratio of 5 to 6 was i nfluenced by the substituent at the C-1 position of the ketone 3. Chir al ketones 3 were transformed into the chiral alpha,beta-unsaturated k etones 5 without racemization.