53907-72-5Relevant articles and documents
Stereocontrolled concise synthesis of (±)-halosaline through intramolecular C-H amination
Meng, Chun-Yan,Liang, Xiao,Zhang, Hongbin,Wei, Kun,Yang, Yu-Rong
, p. 1781 - 1783 (2019)
Total synthesis of 2-(2-hydroxyalkyl)-piperidine alkaloid (±)-halosaline is described from 7-octen-4-ol using a Rh-catalyzed chemo- and diastereo-selective intramolecular C–H amination of sulfamate ester, ring-closing metathesis, and SN2 displa
Generation of allylic manganates from trimethylmanganate and allylic stannanes and their reactions with epoxides
Tang, Jun,Yorimitsu, Hideki,Kakiya, Hirotada,Inoue, Rie,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 9019 - 9022 (2007/10/03)
A new method for forming allyldimethylmanganate has been developed. The preparation eliminated the need for prior generation of an allylmetal species such as allyllithium or allylmagnesium compounds. The reagents reacted with epoxides to give allylated products exclusively in good yields.
Applications of Intramolecular Amidomercuration. 2. Synthesis of trans-5-Hydroxy-2-propylpiperidine, (+/-)-Pseudoconhydrine
Harding, Kenn E.,Burks, Stephen R.
, p. 40 - 44 (2007/10/02)
A method for the stereoselective conversion of δ-alkenyl carbamates into trans-2-alkyl-5-substitutes-piperidines utilizing intramolecular amidomercuration as key step has been developed.As a specific illustration of the method, a synthesis of one of the Hemlock alkaloids, (+/-)-Pseudoconhydrine (trans-5-hydroxy-2-propylpiperidine, 1) was completed.The organomercurial 7a obtained from the intramolecular amidomercuration of 4--7-octene (6) was converted to the corresponding trans-5-(iodomethyl)-2-propylpyrrolidine derivative 7b.Cleavage of the carbamate and treatment with base generated the bicyclic aziridine 2-exo-propyl-1-azabicyclohexane (8a).Treatment of this aziridine with excess trifluoroacetic acid gave ring opening to the disubstituted pyrrolidine derivative 9a exclusively.Ring opening of the analogous aziridine 8b with HCl gave mixtures of pyrrolidine 9b and piperidine 10b.However, these derivatives can be equilibrated through the neutral amine to a mixture consisting of ca. 85percent of the piperidine derivate.Slow addition of trifluoroacetic acid to the aziridine 8a allowed for equilibration to the piperidine 14 as the major product.Hydrolysis and purification gave pure racemic pseudoconhydrine.This sequence illustrates a synthetic equivalent to anti-Markovnikov cyclofunctionalization of δ-alkenyl carbamates.In addition, this study provided new information on the regiochemistry of ring opening bicyclic aziridines.