74608-19-8Relevant academic research and scientific papers
Synthesis of vicinal aminoalcohols by stereoselective aza-wacker cyclizations: Access to (-)-acosamine by redox relay
Weinstein, Adam B.,Schuman, David P.,Tan, Zhi Xu,Stahl, Shannon S.
supporting information, p. 11867 - 11870 (2013/11/19)
Diastereoselective aza-Wacker cyclization of O-allyl hemiaminals under aerobic conditions enables efficient access to 1,2-aminoalcohol derivatives from allylic alcohols. The scope of this method is presented and its utility is highlighted in a streamlined
Intermolecular amination of allyl alcohols with sulfamates: Effective utilization of mercuric catalyst
Yamamoto, Hirofumi,Ho, Elisabeth,Sasaki, Ikuo,Mitsutake, Mizuho,Takagi, Yuichi,Imagawa, Hiroshi,Nishizawa, Mugio
supporting information; experimental part, p. 2417 - 2420 (2011/06/10)
Herein, we describe the intermolecular amination of allyl alcohols with sulfamates, which have been underutilized as nitrogen nucleophiles for allylic amination. Methyl sulfamate is a good nucleophile in the presence of mercuric triflate and efficiently generates monoallylation products in excellent yield at room temperature. Furthermore, the solid-supported mercuric catalyst silaphenyl mercuric triflate also showed remarkable catalytic activity for the allylic amination. Intermolecular amination of allyl alcohol with sulfamate as a modifiable nitrogen nucleophile is presented. Mercuric reagents act as highly efficient catalyst for the allylic amination, and the procedure was applied to the preparation of various amine derivatives. In many cases, the reaction can be carried out at room temperature and is applicable to a large range of allylic alcohols to give the monoallylated products in excellent yield. Copyright
Gold versus silver-catalyzed intermolecular hydroaminations of alkenes and dienes
Giner, Xavier,Najera, Carmen,Kovacs, Gabor,Lledos, Agusti,Ujaque, Gregori
experimental part, p. 3451 - 3466 (2012/02/04)
Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines such as p-nitroaniline, whereas for conjugated dienes carbamates can also be used. Carbon-carbon double bond isomerization is observed only with gold similarly to when triflic acid was used, affording mixtures of regioisomeric products in the same cases. Silver-catalyzed hydroaminations failed with terminal alkenes, except with styrenes. Conjugate dienes can be hydroaminated either at 85 °C in toluene or at room temperature in dichloromethane. Non-conjugated 1,4- and 1,5-dienes suffer double hydroamination leading to saturated N-tosylated heterocyclic amines The catalytic cycle for the silver(I)-catalyzed hydroamination process has been computationally analyzed, resembling gold(I)-catalyzed processes, although with some significant differences. Copyright
Silver-catalyzed intermolecular hydroamination of alkenes and 1,3-dienes
Giner, Xavier,Najera, Carmen
experimental part, p. 3211 - 3213 (2010/04/03)
Silver triflate is used as efficient catalyst for the intermolecular addition of 4-toluenesulfonamide to alkenes under thermal or microwave heating. The hydroamination of 1,3-dienes can be performed at 85 °C with low catalyst loading (0.1-5 mol%) or at room temperature using 1 mol% of AgOTf, the use of HOTf affording similar results.
Synthesis of N-Protected Amino Esters via Palladium Catalysed Allylic Substitution
Jumnah, Roshan,Williams, Jonathan M. J.,Williams, Andrew C.
, p. 6619 - 6622 (2007/10/02)
N-protected allylamines were prepared by palladium catalysed allylic substitution of the corresponding allyl acetates with a range of nitrogen nucleophiles.The so-formed N-protected allylamines were subjected to oxidative cleavage of the alkene to afford N-protected amino acids or esters.
The Chemistry of Sulfur Diimides, 8. - Ene Reactions with Sulfur Diimides - Structure of the Ene Components and Reactivity in the Reaction with Ditosyl Sulfur Diimide
Bussas, Reinhard,Kresze, Guenter
, p. 629 - 649 (2007/10/02)
N,N'-Ditosyl sulfur diimide (1) is an exceptionally reactive enophilic compound.Its reactions with many allylic derivatives give sulfinamidines 3 or - by sigmatropic rearrangements of 3 - diamino sulfane derivatives 4, respectively, in good yields.Conclus
