35351-33-8Relevant articles and documents
Study of the Rearrangements of Oxonium Ylides Generated from Ketals
Brogan, John B.,Zercher, Charles K.,Bauer, Gary B.,Rogers, Robin D.
, p. 3902 - 3909 (1997)
Intramolecular exposure of cyclic ketals to metal carbenoids generates a proposed oxonium ylide intermediate that subsequently rearranges to one of three general products. The product resulting from a 1,2-shift to the ketal carbon is favored by larger ketals that lack radical stabilizing groups. A bridged bicyclic structure is formed by competitive 1,2-shift to the exocyclic carbon of the ketal and is favored by smaller ketal ring sizes that possess radical-stabilizing groups. An alternative β-elimination pathway can also operate when neither of the 1,2-shift pathways are favored. The enol ether that is formed in this latter pathway rearranges easily to an isomeric dioxene.
Convenient preparation of cyclic acetals, using diols, TMS-source, and a catalytic amount of TMSOTf
Kurihara, Masaaki,Hakamata, Wataru
, p. 3413 - 3415 (2007/10/03)
With use of diol, alkoxysilane, and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf), carbonyl compounds are converted to acetals in good yields under mild conditions. This procedure, which was carried out without synthesizing the silylated diols, is a more convenient adaptation of Noyori's method. This acetalization applies to not only simple but also conjugated carbonyl compounds. Moreover, various TMS compounds, including solid supported compounds, are effective for this method instead of alkoxylsilane.
Total synthesis of Cacalol
Garofalo, Albert W.,Litvak, Joane,Wang, Lisa,Dubenko, Larisa G.,Cooper, Raymond,Bierer, Donald E.
, p. 3369 - 3372 (2007/10/03)
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