84319-68-6Relevant academic research and scientific papers
Vinyl Weinreb amides: A versatile alternative to vinyl ketone substrates for the Heck arylation
Baker, David B.,Gallagher, Peter T.,Donohoe, Timothy J.
, p. 3690 - 3697 (2013/05/08)
This paper describes the use of unsaturated Weinreb amides as excellent substrates for the Heck reaction. Subsequent derivatization of the products with organometallic reagents allowed access to a variety of substituted vinyl ketones that could not have been prepared directly via Heck reaction on unsaturated ketone precursors.
Highly efficient Pd-catalyzed carbonylative cross-coupling reactions with tetraorganoindates
Lee, Sung Wook,Lee, Kooyeon,Seomoon, Dong,Kim, Sundae,Kim, Hyunseok,Kim, Hyun,Shim, Eunkyong,Lee, Miae,Lee, Seokju,Kim, Misook,Lee, Phil Ho
, p. 4852 - 4855 (2007/10/03)
Tetraorganoindates, which were prepared easily from the reaction of 1 equiv of InCl3 with 4 equiv of organometallics, could be employed as effective nucleophilic cross-coupling partners in Pd-catalyzed carbonylative cross-coupling reactions with a variety of organic electrophiles. The present method gave unsymmetrical ketones and 1,4-diacylbenzenes in good yields with highly efficient transfer of almost all the organic groups attached to the indium under a carbon monoxide atmosphere in THF at 60 °C.
Titanium-mediated diastereoselective formation of (E)- or (Z)-2-substituted 1-vinylcyclopropanols: Scope and limitation, applications
Racouchot, Sandrine,Sylvestre, Isabelle,Ollivier, Jean,Kozyrkov, Yuri Yu.,Pukin, Alexei,Kulinkovich, Oleg G.,Salauen, Jacques
, p. 2160 - 2176 (2007/10/03)
Titanium-mediated cyclopropanation of α,β-unsaturated esters failed to provide 1-vinylcyclopropanol derivatives in useful yields, but (E)-2-substituted-1-vinylcyclopropanols were formed diastereoselectively from O-protected β-oxo- and β-halo esters, with the allylic double bond being created subsequently (Knoevenagel condensation or dehydrohalogenation). Titanium-mediated cyclopropanation of homoallyl alk-2-enoates, on the other hand, directly provided the corresponding Z diastereomers. Palladium(0)-catalysed azidation of their sulfonic esters (tosylate, mesylate), azide reduction, and subsequent double bond cleavage afforded (E)- or (Z)-2-alkyl-2,3-methanoamino acids, although improvements are required to perform the total asymmetric syntheses of molecules with three membered-rings by these methods. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Organocuprates Containing Dimethyl Sulfoxide Anion as a Nontransferable Ligand
Johnson, Carl R.,Dhanoa, Daljit S.
, p. 1885 - 1888 (2007/10/02)
Mixed homocuprates and in which the anion of dimethyl sulfoxide acts as a nontransferable ligand are readily prepared from MeSOCH2Li, alkyl- or aryllithium reagents, and Cu(I) salts.These novel cuprates are useful in the conversions of acid chlorides to ketones, conjugate additions to α,β-unsaturated ketones, SN2' reactions with allylic or propargylic acetates and epoxides, and coupling reactions with primary iodides and tosylates.All of these reactions proceed with selective transfer of the ligand R.From the points of view of cost, availability, and lack of interference with product isolation, the Me2SO anion is an ideal nontransferable ligand.
