934472-06-7Relevant articles and documents
One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step
Hayashi, Yujiro,Urushima, Tatsuya,Sakamoto, Daisuke,Torii, Kou,Ishikawa, Hayato
, p. 11715 - 11718 (2011/11/06)
Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).
Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A
Mancey, Nicole C.,Sandon, Nicolas,Auvinet, Anne-Laure,Butlin, Roger J.,Czechtizky, Werngard,Harrity, Joseph P. A.
, p. 9804 - 9806 (2011/10/11)
The enantiospecific and diastereocontrolled total synthesis of alkaloid (-)-217A is described that employs a stepwise [3+3] annelation strategy and a piperidine 2,3-cyclopropanation-ring opening reaction as the key steps.
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.