Efficient and practical method for synthesizing optically active indan-2-ols by the Ti(O-i-Pr)4/2 i-PrMgCl-mediated metalative Reppe reaction
An efficient and practical synthesis of optically active indan-2-ols 1 has been developed starting from readily accessible optically active 4-siloxy-1,6-alkadiynes 2 and ethynylp-tolyl sulfone, where the metalative Reppe reaction mediated by an economical divalent titanium reagent, Ti-(O-i-Pr)4/2 i-PrMgCl, is a key step.
Regiochemical and Stereochemical Studies on Halogen-Induced Ring Expansions of Unsaturated Episulfides
The reactions of unsaturated episulfides with bromine and iodine have been studied.Initially produced in the reaction is a ring-opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to β,β'-dihalo sulfide cycloadducts.The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation.A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.
Ren, Xiao-Feng,Konaklieva, Monika I.,Turos, Edward,Krajkowski, Lynn M.,Lake, Charles H.,et al.
p. 6484 - 6495
(2007/10/03)
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