Gold-catalyzed oxidative ring expansions and ring cleavages of alkynylcyclopropanes by intermolecular reactions oxidized by diphenylsulfoxide
A golden opportunity: A novel gold-catalyzed oxidative ring-expansion of unactivated cyclopropylalkynes using Ph2SO has been developed (see scheme). For substrates bearing a donor group at the cyclopropane ring, preliminary results reveal a distinct cleavage of the cyclopropane unit; such a ring cleavage is further applicable to the synthesis of 2H-pyrans. L=P(tBu) 2(o-biphenyl), Tf=triflate. Copyright
An improved synthesis of cyclopropanes from homoallenic alcohols
Treatment of the readily available β-allene tosylates with LDA or nBuLi provides an expeditious, although stereorandom, synthesis of functionalized cyclopropanes which can be easily prepared in high enantiomeric purity.
Pyo, Sungsoo,Skowron III, Joseph F.,Cha, Jin K.
p. 4703 - 4706
(2007/10/02)
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