131379-29-8Relevant academic research and scientific papers
Iridium-catalyzed enantioselective allylic alkylation with functionalized organozinc bromides
Hamilton, James Y.,Sarlah, David,Carreira, Erick M.
, p. 7644 - 7647 (2015)
Iridium-catalyzed enantioselective allylic alkylation of branched racemic carbonates with functionalized alkylzinc bromide reagents is described. Enabled by a chiral Ir/(P,olefin) complex, the method described allows allylic substitution with various primary and secondary alkyl nucleophiles with excellent regio- and enantioselectivities. The developed reaction was showcased in a concise, asymmetric synthesis of (-)-preclamol. An Ir/(P,olefin) complex catalyzes the title reaction and the method provides a variety of allylated products with excellent regio- and stereoselectivities. The utility of the coupling is demonstrated in a catalytic enantioselective synthesis of a preclinical drug (-)-preclamol. Boc=tert-butyloxycarbonyl, cod=1,5-cyclooctadiene.
Highly reactive forms of zinc and reagents thereof
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, (2008/06/13)
A novel zerovalent zinc species and an organozinc reagent are disclosed. The zerovalent zinc species is directly produced by reaction of a reducing agent on a zinc salt, preferably Zn(CN)2. The organozinc reagent results from the reaction of the zerovalent zinc species and an organic compound having one or more stable anionic leaving groups. These organozinc reagents include a wide spectrum of functional groups in the organic radical, and are useful in a variety of reactions schemes.
The Direct Formation of Functionalized Alkyl(aryl)zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid Chlorides, α,β-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides
Zhu, Lishan,Wehmeyer, Richard M.,Rieke, Reuben D.
, p. 1445 - 1453 (2007/10/02)
Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields.Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides.Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds.In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to α,β-unsaturated ketones, and regioselectively undergo SN2' substitution reactions with allylic halides.They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.
