Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton

Article abstract of DOI:10.1016/0040-4020(95)01005-X

The new chiral nonracemic homoallylic exo-alcohols 6, 7, 10 with (1R)-(+)-camphor (1) and endo-alcohols 8, 9, 11 with (1R)-(-)-fenchone (2) skeleton were synthesized in high yields by the stereoselective addition of allyl and substituted allylic Grignard reagents 3-5 to 1 and 2, respectively. The addition of the 2-butenyl (crotyl) reagent 5 occurred with high selectively leading exclusively to α-methylallyl alcohol 10 with ketone 1 and to (Z)-2-butenyl alcohol 11 with ketone 2. The absolute configurations of the homoallylic alcohols 6-11 were determined by NMR methods.