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Keywords = sulfinyl imines

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16 pages, 2631 KiB  
Article
Stereoselective Synthesis of 1-Substituted Homotropanones, including Natural Alkaloid (−)-Adaline
by Sandra Hernández-Ibáñez, Ana Sirvent, Miguel Yus and Francisco Foubelo
Molecules 2023, 28(5), 2414; https://doi.org/10.3390/molecules28052414 - 6 Mar 2023
Cited by 3 | Viewed by 2782
Abstract
The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with [...] Read more.
The stereocontrolled synthesis of 1-substituted homotropanones, using chiral N-tert-butanesulfinyl imines as reaction intermediates, is described. The reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with β-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization are key steps of this methodology. The utility of the method was demonstrated with a synthesis of the natural product (−)-adaline, and its enantiomer, (+)-adaline. Full article
(This article belongs to the Special Issue A Journey of Organic Chemistry in Spain)
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15 pages, 1756 KiB  
Article
Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
by Ana Sirvent, Francisco Foubelo and Miguel Yus
Molecules 2021, 26(21), 6503; https://doi.org/10.3390/molecules26216503 - 28 Oct 2021
Cited by 4 | Viewed by 2731
Abstract
The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of [...] Read more.
The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)- and (−)-isosolenopsin A. Full article
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