Helvetica Chimica Acta p. 1281 - 1287 (1994)
Update date:2022-08-03
Topics:
Hoskovec, Michal
Koutek, Bohumir
Lazar, Josef
Streinz, Ludvik
Brozova, Eva
et al.
The two-step alkylation of phenyl prop-2-enyl sulfone (1) with protected ω-bromoalkanols and 1-iodoalkanes (-> 3: see Scheme 1) followed by a Pd-catalyzed desulfonylation with LiBH4 affords a 96:4 mixture of vinyl-branched, protected alcohols and corresponding ethylidene-branched isomers (see Scheme 2; 4 and 5, respectively).By utilizing the large difference in reactivity of mono- and trisubstituted C=C bonds towards singlet oxygen, the ethylidene derivatives are easily removed from the mixture by photo-oxygenation.The vinyl-branched compounds are inert to this reaction and can be conveniently isolated in highly pure form (99.5percent) and ca. 45percent overall yield.
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Doi:10.1016/0008-6215(94)84179-9
(1994)Doi:10.1021/jo00094a005
(1994)Doi:10.1080/15257779408011881
(1994)Doi:10.1080/00397919608003533
(1996)Doi:10.1002/ardp.201100345
(2012)Doi:10.1021/ol5009119
(2014)
