60343-68-2Relevant academic research and scientific papers
Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Allenes
Berthold, Dino,Geissler, Arne G. A.,Giofré, Sabrina,Breit, Bernhard
supporting information, p. 9994 - 9997 (2019/07/04)
The rhodium-catalyzed asymmetric intramolecular hydroamination of sulfonyl amides with terminal allenes is reported. It provides selective access to 5- and 6-membered N-heterocycles, scaffolds found in a large range of different bioactive compounds. Moreover, gram scale reactions, as well as the application of suitable product transformations to natural products and key intermediates thereof are demonstrated.
An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids
Bisai, Alakesh,Singh, Vinod K.
, p. 1907 - 1910 (2007/10/03)
We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.
Asymmetric piperidine synthesis via 1,3-cyclic sulfates
Eskici,Gallagher
, p. 1360 - 1362 (2007/10/03)
Cyclic sulfates undergo a double alkylation with stabilized C,N-dianions derived from 3a/b to provide the piperidine ring system. The 4-substituted variant 7 affords a formal but stereochemically efficient synthesis of (S)-coniine.
