- A cascade Aza-Cope/Aza-prins cyclization leading to piperidine derivatives
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The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin. The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines is described. A unimolecular tetrapiperidine derivative, which resulted from this strategy, was employed as a ligand in the Suzuki-Miyaura cross-coupling reaction of an α-iodobutenolide with an arylboronic acid in an efficient synthesis of incrustoporin and its analogues.
- Nallasivam, Jothi L.,Fernandes, Rodney A.
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p. 2012 - 2022
(2015/03/18)
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- A simple method to prepare homoallylic amines from secondary homoallylic mesylates
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The nucleophilic substitution by primary amines of secondary homoallylic mesylates easily obtained from corresponding alcohols offers a convenient way to prepare homoallylic amines. The relative low yields in pure compounds is counterbalanced by the simpl
- Henin,Mahuet,Muller,Muzart
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p. 1331 - 1338
(2007/10/02)
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- Stereoselective Synthesis of 2,6-Disubstituted Piperidine Alkaloids via TiCl4 Induced Iminium Ion Cyclization of α-Cyanoamines
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The stereoselective cyclization of an α-cyanoamine containing a vinyl group induced by TiCl4 in a methylene chloride solution, produces cis 2,6-dialkylpiperidine; whereas a similar reaction of an α-cyanoamine containing a silyl substituted vinyl group gav
- Yang, Teng-Kuei,Teng, Tsung-Fan,Lin, Jyh-Hwa,Lay, Yen-Yuan
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p. 3581 - 3582
(2007/10/02)
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