187974-79-4Relevant academic research and scientific papers
'meso-Selective' functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation
Bragg, Ryan A,Clayden, Jonathan,Menet, Christel J
, p. 1955 - 1959 (2002)
Lithiation and methylation of amide and carbamate derivatives of α-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-α-methylbenzylamine derivatives. Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-α-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability.
Nickel-catalyzed allylation of α-amido sulfones to form protected homoallylic amines
Caputo, Jill A.,Naodovic, Marina,Weix, Daniel J.
, p. 323 - 326 (2015)
The allylation of stable, protected imine precursors, α-amido sulfones, with allylic acetates to form homoallylic amines is catalyzed by nickel under mild reducing conditions. Aliphatic and aryl imines are tolerated, as are substituted allylic acetates. I
The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines
Carrera, Diane E.
supporting information, p. 11185 - 11188 (2017/10/16)
The acid promoted addition of organotrifluoroborate salts to imine and enamine electrophiles is reported. Use of the pre-activated trifluoroboronate complex bypasses the need for α-hetero substitution on the electrophile component, greatly expanding the scope of the Petasis borono-Mannich reaction. A variety of vinyl, aromatic and heteroaromatic trifluoroborate salts undergo addition with good efficiency under mild reaction conditions. The reaction is amenable for use with a variety of carbamate protected imine and enamine electrophiles, achieving for the first time the effective coupling with aliphatic aldehydes.
Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions
Peterson, Luke J.,Luo, Jingyi,Wolfe, John P.
supporting information, p. 2817 - 2820 (2017/06/07)
Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.
Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms
Lang, Simon B.,O'Nele, Kathryn M.,Douglas, Justin T.,Tunge, Jon A.
, p. 18589 - 18593 (2016/01/25)
The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
Pd(II)-catalyzed allylic C-H amination for the preparation of 1,2- and 1,3-cyclic ureas
Nishikawa, Yasuhiro,Kimura, Seikou,Kato, Yuri,Yamazaki, Natsuka,Hara, Osamu
, p. 888 - 891 (2015/03/18)
A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)2/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.
N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation
Osberger, Thomas J.,White, M. Christina
supporting information, p. 11176 - 11181 (2014/08/18)
A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
Allylation of n,n-acetal derivatives using allyl tin reagent in the presence of aluminum chloride
Sun, Xiaonan,Obu, Takanori,Kijima, Tatsuro,Murakami, Satoshi,Matsuba, Shigeru,Kusakari, Miho,Hatano, Bunpei
, p. 2395 - 2402 (2013/11/19)
Allylation of N,N-acetal derivatives proceeded efficiently using allyl tin regent in the presence of aluminum chloride, giving homoallylamines in good yields. This allylation was applied for N,S-acetals to give the corresponding homoallylamines.
A new method of synthesis of 6-substituted piperidine-2,4-diones from homoallylamines
Kuznetsov, Nikolai Yu.,Maleev, Victor I.,Khrustalev, Victor N.,Mkrtchyan, Anna F.,Godovikov, Ivan A.,Strelkova, Tatyana V.,Bubnov, Yuri N.
, p. 334 - 344 (2012/02/16)
Mono- and dihomoallylamines serve as convenient precursors for the preparation of 6-substituted piperidine-2,4-diones. This transformation is based, on the one hand, on a simple and well-known halocyclocarbamation reaction proceeding by the addition of a
A Hg(ClO4)2 3 3H2O Catalyzed sakurai-hosomi allylation of isatins and isatin ketoimines using allyltrimethylsilane
Cao, Zhong-Yan,Zhang, Yan,Ji, Cong-Bin,Zhou, Jian
supporting information; experimental part, p. 6398 - 6401 (2012/02/02)
It is reported that Hg(ClO4)2 3 3H2O could efficiently activate the cheap but less reactive allyltrimethylsilane for the allylation of isatins or isatin ketoimines, with catalyst loading down to 0.1 mol %. This is the firs
