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Borane reactions XI : The transformation of α,β-unsaturated ketones into 3-alkyl-trans-1,2-diols.

✍ Scribed by J. Klein; R. Levene; E. Dunkelblum

Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 121 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)94228-5

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✦ Synopsis

Conjugate addition of alkylwhgwl~ derIvatIvea 2.3) and that of dialkylcopper lithlu~~~~) unoutlLlyxedorcatalyeedbyqroluealte, to oonju@edketanee, leade to 3-elQlkeWo. Intmduotioe of8llac8toxy (Ppup~ totheoarbonylinl~~by fYJ4ugateadditifmofDet4l4pdubrmi& aud eubeeqwhtPb(OAc)4 oxidation hae beenrap~rted~). We drh to mpert a Iljatlmt$o mtbd i9mt girsn directly Wl-oyclohexane-&ll&l,&diole etfuting irocr 2--e.

Addition of 2-oyolohe%moM todhetl@oopperllthhm 5, (W exoeee) im ether at -100 duriq 15lin. and decoqodtion of the reactionmlduredth diluteEl at-loo&am ~~l~@oh~ in %$ Held. Thie reaotionrircUrewae treated, before acidification, with a eolution ofbonum in THF (3 mlee per mole ketone) for 3 houm at ro~(p tapemtum.

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