60123-29-7Relevant academic research and scientific papers
Catalytic Metal-free Allylic C?H Amination of Terpenoids
Teh, Wei Pin,Obenschain, Derek C.,Black, Blaise M.,Michael, Forrest E.
, p. 16716 - 16722 (2020)
The selective replacement of C?H bonds in complex molecules, especially natural products like terpenoids, is a highly efficient way to introduce new functionality and/or couple fragments. Here, we report the development of a new metal-free allylic amination of alkenes that allows the introduction of a wide range of nitrogen functionality at the allylic position of alkenes with unique regioselectivity and no allylic transposition. This reaction employs catalytic amounts of selenium in the form of phosphine selenides or selenoureas. Simple sulfonamides and sulfamates can be used directly in the reaction without the need to prepare isolated nitrenoid precursors. We demonstrate the utility of this transformation by aminating a large set of terpenoids in high yield and regioselectivity.
Synthesis and reactions of organic compounds with a nitrogen atom. Part XII. Toluenesulfonamidation of (+)-2-carene and synthesis of amines and aminoalcohols of the carane group
Uzarewicz,Scianowski
, p. 48 - 51 (2007/10/03)
Toluenesulfonamidation of (+)-2-carene 2 afforded: 4-methyl-N-trans-(2-caren-4-yl) benzenesulfonamide 3 and 4-methyl-N-(2-caren-10-yl)benzenesulfonamide 4, which were converted by the reduction with sodium in liquid ammonia to: (-)-trans-4-amino-2-carene
Synthesis and Reactions of Organic Compounds with a Nitrogen Atom. Part X. Synthesis of Allylic 1,2-Ditoluenesulfonamide, 1,2-Diamine, Hydroxy-1,2-ditoluenesulfonamide and Hydroxy-1,2-diamine from (+)-α-Phellandrene
Uzarewicz, A.,Wyzlic, I.,Scianowski, J.
, p. 681 - 684 (2007/10/02)
Toluenesulfonamidation of (+)-α-phellandrene afforded 4-methyl-N-(1'-p-menthen-5'r,6'c-diyl)dibenzenesulfonamide 6 which was reduced by sodium in liquid ammonia to give the diamine 7.Hydroboration-oxidation of 6 followed by the sodium/ammonia reduction ga
Synthesis and Reactions of Organic Compounds with a Nitrogen Atom. Part XI. The Reaction of Limonene with Bis(p-toluenesulfonyl)selenodiimide
Uzarewicz, A.,Scianowski, J.,Wyzlic, I.
, p. 1153 - 1157 (2007/10/02)
Toluenesulfonamidation of (S)-(-)-limonene, (R)-(+)-limonene and dipentene gave (+/-)-4-methyl-N-benzenesulfonamide 8.Additionally (S)-(-)-limonene, (R)-(+)-limonene afforded the corresponding enantiomers of 4-methyl-N-1',7'(8
A [3 + 2] and [4 + 3] cycloaddition approach to N-heterocycles via Pd-catalyzed TMM reactions with imines
Trost, Barry M.,Marrs, Christopher M.
, p. 6636 - 6645 (2007/10/02)
The question of cycloadditions of (trimethylenemethane) palladium complexes to heteroation is probed in the context of pyrrolidine syntheses. Whereas simple imines fail to react, imines possessing an electron-withdrawing group at either the carbon or nitrogen enhance the electrophilicity of the imine sufficiently to make it an excellent accetor. Palladium(0) complexes catalyze cycloadditions of 2-((trimethylsilyl)methyl)allyl esters to N-tosyl- and N-nitroimines. The stronger electron-withdrawing nature of the nitre group permits nitrimines derived from relatively hindered ketones to participate. Conjugated cisoid imines lead to [4 + 3] cycloadditions - a process azepine synthesis. Substituted TMM precursors cycloadd with high regioselectivity. The result. are consistent with a two-step addition process. Some of the simple examples explored to determine the scope and limitations of the process reveal simple syntheses of proline and nicotine analogues. The successful employment of imines as direct acceptors for TMM-PdL2 opens a new chapter on metal-catalyzed cycloadditions.
SYNTHESIS AND REACTIONS OF ORGANIC COMPOUNDS WITH A NITROGEN ATOM. PART IV. SYNTHESIS AND REACTIONS OF (-)-TRANS-2-AMINO-3-CARENE AND (+)-10-AMINO-3-CARENE
Wyzlic, Iwona,Uzarewicz, Arkadiusz
, p. 1999 - 2004 (2007/10/02)
The toluenesulfonamidation of (+)-3-carene afforded two toluenesulfonamides, which were converted by reduction with sodium in liquid ammonia to (-)-trans-2-amino-3-carene and (+)-10-amino-3-carene, respectively.The hydroboration-oxidation of these amines
SYNTHESIS AND REACTIONS OF ORGANIC COMPOUNDS CONTAINING NITROGEN ATOM. PART I. SYNTHESIS AND REACTIONS OF 10-AMINO-2-PINENE AND TRANS-3-AMINO-2(10)-PINENE
Wyzlic, Iwona,Uzarewicz, Ireneusz G.,Uzarewicz, Arkadiusz
, p. 113 - 121 (2007/10/02)
The toluenesulfonamidation of (+)-, (-)-2-pinenes and (-)-2(10)-pinene afforded toluenesulfonamides, which were converted by reduction with sodium in liquid ammonia to the corresponding amines: 10-amino-2-pinenes and trans-3-amino-2(10)-pinene.The hydrobo
Syntheses of Biologically Important Carbohydrates, 21. Asymmetrically Induced Synthesis of Amino Sugars: Methyl 4-O-Acetyl-3-acetylamino-2,3,6-trideoxy-α-D-xylo-hexopyranoside
Dyong, Ingolf,Wiemann, Reinhard
, p. 1592 - 1602 (2007/10/02)
trans-4-Hexenal-((2R,3R)tartaric acid dimethyl ester acetal) (6) is aminated in allylic position with metallic selenium and chloramine-T yielding the easily separable 3-tosylamino derivatives with D-(7) and L-glycero-configuration (8) at C-3. 7 is hydoxyl
