15991-59-0Relevant articles and documents
Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate
Satyalakshmi, Gandham,Suneel, Kanaparthy,Shinde, Digambar Balaji,Das, Biswanath
, p. 1000 - 1005 (2011)
The stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine and (+)-sedamine has been achieved through a common intermediate generated from butane-1,4-diol. The synthetic sequence involves a Maruoka asymmetric allylation and ring-closing metathesis as the key steps.
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.
A direct and general method for the reductive alkylation of tertiary lactams/amides: Application to the step economical synthesis of alkaloid (-)-morusimic acid D
Xiao, Kai-Jiong,Wang, Yu,Huang, Ying-Hong,Wang, Xiao-Gang,Huang, Pei-Qiang
, p. 8305 - 8311 (2013/09/24)
Full details of the direct and general method for the reductive alkylation of tertiary lactams and amides to give tertiary sec-alkylamines are presented. This one-pot method consists of in situ activation of a lactam or an amide with Tf2O/DTBMP, addition of a Grignard reagent, and reduction of the resulting iminium intermediates. Alkyl, benzyl, and aryl Grignard reagents and several reductants or reducing conditions (LiAlH4, NaBH4, Hantzsch ester, Bu3SnH, Pd(OH)2/C, H2) could be used effectively. Reductive alkylations of substituted lactams demonstrated good to excellent 1,3-asymmetric induction to provide the corresponding di- or trisubstituted pyrrolidine/piperidine in 6:1 (LiAlH4), 11:1 (Et 3SiH), and 20:1 (catalytic hydrogenation) cis/trans diastereoselectivity, respectively. The versatility of this methodology was demonstrated by its application in the concise stereoselective synthesis of piperidine alkaloid (-)-morusimic acid.