Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (−)-fenchone skeleton
1996; Elsevier BV; Volume: 52; Issue: 5 Linguagem: Inglês
10.1016/0040-4020(95)01005-x
ISSN1464-5416
AutoresVladimir Dimitrov, Svetlana Simova, Kalina Kostova,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoThe 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 selectivity 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.
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