75950-58-2Relevant academic research and scientific papers
Cu-Catalyzed highly regioselective 1,2-hydrocarboxylation of 1,3-dienes with CO2
Zhang, Penglin,Zhou, Zhanglang,Zhang, Rumeng,Zhao, Qian,Zhang, Chun
supporting information, p. 11469 - 11472 (2020/10/12)
A practical copper-catalyzed highly regioselective 1,2-hydrocarboxylation of terminal 1,3-diene with carbon dioxide has been developed. Under mild reaction conditions, this chemistry afforded 2-benzyl-β,γ-unsaturated acid derivatives as products, which are a kind of important unit for bio-active molecules and versatile precursors for organic synthesis, with good functional group tolerance. The key intermediate in this transformation is illustrated by control experiments.
Reversible C-C bond activation enables stereocontrol in Rh-catalyzed carbonylative cycloadditions of aminocyclopropanes
Shaw, Megan H.,McCreanor, Niall G.,Whittingham, William G.,Bower, John F.
supporting information, p. 463 - 468 (2015/01/30)
Upon exposure to neutral or cationic Rh(I)-catalyst systems, amino-substituted cyclopropanes undergo carbonylative cycloaddition with tethered alkenes to provide stereochemically complex N-heterocyclic scaffolds. These processes rely upon the generation and trapping of rhodacyclopentanone intermediates, which arise by regioselective, Cbz-directed insertion of Rh and CO into one of the two proximal aminocyclopropane C-C bonds. For cyclizations using cationic Rh(I)-systems, synthetic and mechanistic studies indicate that rhodacyclopentanone formation is reversible and that the alkene insertion step determines product diastereoselectivity. This regime facilitates high levels of stereocontrol with respect to substituents on the alkene tether. The option of generating rhodacyclopentanones dynamically provides a new facet to a growing area of catalysis and may find use as a (stereo)control strategy in other processes.
Construction of tetrahydrofurans by PdII/PdIV- catalyzed aminooxygenation of alkenes
Desai, Lopa V.,Sanford, Melanie S.
, p. 5737 - 5740 (2008/04/12)
(Chemical Equation Presented) Resolute in the face of elimination: Substituted 3-aminotetrahydrofurans were prepared in good yield and with modest to high diastereoselectivity by the Pd-catalyzed reaction shown in the scheme (Phth = phthaloyl). Mechanisti
Reagent-controlled stereoselective synthesis of lignan-related tetrahydrofurans
Miles, Steven M.,Marsden, Stephen P.,Leatherbarrow, Robin J.,Coates, William J.
, p. 6874 - 6882 (2007/10/03)
The reaction of ring-closing metathesis-derived cyclic allylsiloxanes 3 with aldehydes in the presence of a Lewis acid gives 2,3,4-trisubstituted tetrahydrofurans related to the furanolignan family of natural products. The reactions proceed with complete
Diastereoselective cycloadditions of chiral homoallylic alcohols with benzonitrile oxide
Kociolek, Martin G.,Hongfa, Chayanant
, p. 1811 - 1813 (2007/10/03)
The first diastereoselective cycloaddition of a nitrile oxide with a homoallylic alcohol is discussed. The reaction of benzonitrile oxide with the magnesium alkoxides of chiral homoallylic alcohols has been shown to proceed with good diastereoselectivity, favoring the syn isomer of the resulting 2-isoxazoline.
EFFICIENT AND REGIOCONTROLLED NICKEL(II)-CATALYZED ALKYLATION OF 2-ALKYL-1,3-DIOXEP-4-ENES BY GRIGNARD REAGENTS: A SIMPLE ROUTE TO ALLYLIC ALCOHOLS
Malanga, Corrado,Menicagli, Rita,Lardicci, Luciano
, p. 45 - 50 (2007/10/02)
The regio- and the stereochemistries of the NidppeCl2 catalyzed alkylation of 2-alkyl-1,3-dioxep-4-enes by Grignard reagents are not affected by the nature of the C2 substituent; in any case, allylic alcohols are the main reaction products and nearly pure Z isomers are almost quantitatively obtained when either secondary or tertiary Grignard reagents are used.A rationale for the reaction is proposed.
NICKEL(II)-CATALYZED ALKYLATION OF 2-METHYL-1,3-DIOXEP-4-ENE BY GRIGNARD REAGENTS: AN EFFICIENT AND SELECTIVE ROUTE TO ALLYLIC ALCOHOLS
Menicagli, Rita,Malanga, Corrado,Finato, Barbara,Lardicci, Luciano
, p. 69 - 70 (2007/10/02)
Allylic alcohols are formed, in good yields, through the regiocontrolled Cl2Nidppe-catalyzed alkylation of 2-methyl-1,3-dioxep-4-ene by Grignard reagents .Highly pure Z alcohols arise when secondary and tertiary aliphatic Grignards are used.
A CONVENIENT METHOD FOR THE SYNTHESIS OF HOMOALLYL ALCOHOL USING A NEW DESULFONYLATION METHOD
Kotake, Hiroshi,Yamamoto, Taku,Kinoshita, Hideki
, p. 1331 - 1334 (2007/10/02)
2-Tosyl homoallyl alcohol obtained by the reaction of allylic p-tolyl sulfone with aldehyde was found to be easily desulfonylated to homoallyl alcohol by the use of Pd(PPh3)4 as a catalyst and hydride ion as a nucleophile, without any side reactions.
Synthesis of (+/-)-Lavandulol and its Related Homoallylic Alcohol via Allyl Transfer from Sulphur to Tin
Ueno, Yoshio,Aoki, Seiichi,Okawara, Makoto
, p. 683 - 684 (2007/10/02)
(+/-)-Lavandulol and related homoallylic alcohols were prepared by the stannolysis of allylic sulphones and the subsequent hydroxymethylation of the resulting allylic stannanes with trioxan-BF3*OEt2.
