58567-43-4Relevant articles and documents
Synthesizing Molecules with Linear Tricyclic 5/5/5 and 6/5/5 Skeletons via [5 + 2 + 1]/Ene Strategy
Liu, Jing,Zhou, Yi,Zhu, Jiaqi,Yu, Zhi-Xiang
, p. 7566 - 7570 (2021/10/02)
Report here is the development of a [5 + 2 + 1]/ene strategy for the synthesis of molecules with linear tricyclic 5/5/5 and 6/5/5 skeletons widely found in natural products. The first step of this strategy is applying a Rh-catalyzed [5 + 2 + 1] reaction o
Rh(iii)-Catalyzed allylic C-H amidation of unactivated alkenes within situgenerated iminoiodinanes
Jeganmohan, Masilamani,Sihag, Pinki
supporting information, p. 6428 - 6431 (2021/07/02)
Rh(iii)-catalyzed allylic C-H amidation of substituted alkenes within situgenerated iminoiodinanes is demonstrated. The presented protocol is compatible with differently functionalized unactivated terminal alkenes and internal alkenes. In terminal alkenes
Regio- And diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism
Ariga, Elaine Miho,Carita Correra, Thiago,Matsushima, Jullyane Emi,McIndoe, J. Scott,Moreira Ribeiro, Francisco Wanderson,Omari, Isaac,Papa Spadafora, Bruna,Rodrigues, Alessandro,Soares, Priscila Machado Arruda,Vinhato, Elisangela,de Oliveira-Silva, Diogo
, p. 5595 - 5606 (2021/07/02)
The regio- and diastereoselective synthesis of oxazolidinonesviaa Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6?:?1 to >20?:?1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through ananti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed.
Regioselective Cp*Ir(III)-Catalyzed Allylic C-H Sulfamidation of Allylbenzene Derivatives
Kazerouni, Amaan M.,Nelson, Taylor A. F.,Chen, Steven W.,Sharp, Kimberly R.,Blakey, Simon B.
, p. 13179 - 13185 (2019/09/30)
In this study we report the development of the regioselective Cp*Ir(III)-catalyzed allylic C-H sulfamidation of allylbenzene derivatives, using azides as the nitrogen source. The reaction putatively proceeds through a Cp*Ir(III)-π-allyl intermediate and demonstrates exclusive regioselectivity for the branched position of the π-allyl. The reaction performs well on electron-rich and electron-deficient allylbenzene derivatives and is tolerant of a wide range of functional groups, including carbamates, esters, and ketones. The proposed mechanism for this reaction proceeds via C-N reductive elimination from a Cp*Ir(V) nitrenoid complex at the branched position of the π-allyl.
Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage
Fan, Chao,Lv, Xin-Yang,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 2889 - 2893 (2019/02/19)
A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C - C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.
Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity
Susanti, Dewi,Liu, Li-Juan,Rao, Weidong,Lin, Sheng,Ma, Dik-Lung,Leung, Chung-Hang,Chan, Philip Wai Hong
, p. 9111 - 9118 (2015/06/16)
A synthetic method to prepare 3a,6-methanoisoindole esters efficiently by gold(I)-catalyzed tandem 1,2-acyloxy migration/Nazarov cyclization followed by Diels-Alder reaction of 1,4,9-dienyne esters is described. We also report the ability of one example t
Catalytic dicyanative 5-exo- And 6-endo-cyclization triggered by cyanopalladation of alkynes
Arai, Shigeru,Koike, Yuka,Nishida, Atsushi
supporting information; experimental part, p. 893 - 900 (2010/07/06)
A stereoselective dicyanative 5-exo- and 6endo-cyclization using various enynes has been investigated. The mode of cyclization is critically controlled by the structure of the substrates. For example, N-allyl derivatives prefer 5-exo-cyclization, while methacryloyl amides are transformed to the corresponding lactams with tetra substituted carbons at the alpha-position via 6-endo-cyclization. Both reactions include syn-cyanopalladation to carbon≡carbon triple bonds in the initial step, and sequential cyclization followed by reductive elimination in one operation enables the construction of the highly functionalized nitrogen heterocycles. The scope of suitable substrates and a proposed mechanism are also described.
Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: A new catalytic route to β3-amino acids
Weiner, Barbara,Baeza, Alejandro,Jerphagnon, Thomas,Feringa, Ben L.
supporting information; experimental part, p. 9473 - 9474 (2009/12/06)
(Chemical Equation Presented) A new method for the synthesis of β3-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl2 and CuCl or Pd(MeCN)2/s
Palladium-catalyzed allylic transposition of (allyloxy) iminodiazaphospholidines: A formal [3,3]-aza-phospha-oxa-cope sigmatropic rearrangement for the stereoselective synthesis of allylic amines
Lee, Ernest E.,Batey, Robert A.
, p. 14887 - 14893 (2007/10/03)
The synthesis of N-protected allylic amines has been achieved utilizing a palladium(II)-catalyzed, [3,3]-rearrangement of (allyloxy) iminodiazaphospholidines. This [3,3]-aza-phospha-oxa-Cope sigmatropic rearrangement reaction is thermodynamically driven by a P=N to P=O interconversion and is an alternative to the Overman rearrangement. The overall process involves the nucleophilic displacement of an allylic alcohol onto a P(III) precursor, followed by a Staudinger reaction to generate the (allyloxy) iminodiazaphospholidine precursors. Pd(II)-catalyzed [3,3]-aza-phospha-oxa-Cope rearrangement then gives a phosphoramide, which is readily hydrolyzed under acidic conditions to yield allylic amine derivatives. Pd(II) catalysis is believed to occur in a fashion analogous to that of the rearrangement of allylic imidates. The scope of racemic, diastereoselective, and enantioselective variants of this rearrangement is described. The use of chiral diamine auxiliaries in diastereoselective rearrangements is reported. Rearrangement of chiral N,N′-dimethyl cyclohexanediamine derived diazaphospholidines gives rise to phosphoramides with moderate diastereoselectivities (up to 3.5:1 dr). The same major diastereomeric product in these rearrangements was prepared irrespective of the starting allylic alcohol geometry. An enantioselective variant of the reaction was demonstrated for the rearrangement of cis-(allyloxy) iminodiazaphospholidines with cobalt oxazoline palladacycle (COP-X) catalysts (5 mol %) in high yield and enantioselectivity (up to 96% ee).
Introduction of Functionalized C1, C2, and C3 Units to Imines through the Dimethylzinc-Air-Initiated Radical Addition
Yamada, Ken-Ichi,Yamamoto, Yasutomo,Maekawa, Masaru,Tomioka, Kiyoshi
, p. 1531 - 1534 (2007/10/03)
Introduction of functionalized C1, C2, and C3 units to imines was achieved by using the dimethylzinc-air-initiated α-alkoxyalkyl radical addition as a key reaction. The addition to a C= N double bond chemoselectively occurred in the presence of a C=O doub
