Si-based benzylic 1,4-rearrangement/cyclization reaction.
The trans-selective hydrosilylation of ynones (1) yields beta-silylated enones (2) that undergo a benzylic 1,4-rearrangement/cyclization reaction in the presence of base, yielding 2,5-dihydro-1,2-oxasiloles (3).
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Bertogg
Andreas
A
D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001555:Benzene Derivatives; D007659:Ketones; D017646:Organosilicon Compounds