Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds

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 ket...

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Autores principales:	Ana Sirvent, Francisco Foubelo, Miguel Yus
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	chiral sulfinyl imines functionalized organolithium compounds diastereoselective additions piperidine alkaloids isosolenopsin A Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/1abb41bfe87547e09a65eb82a15fb954
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spelling	oai:doaj.org-article:1abb41bfe87547e09a65eb82a15fb9542021-11-11T18:30:06ZStereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds10.3390/molecules262165031420-3049https://doaj.org/article/1abb41bfe87547e09a65eb82a15fb9542021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6503https://doaj.org/toc/1420-3049The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to <i>N</i>-<i>tert</i>-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.Ana SirventFrancisco FoubeloMiguel YusMDPI AGarticlechiral sulfinyl iminesfunctionalized organolithium compoundsdiastereoselective additionspiperidine alkaloidsisosolenopsin AOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6503, p 6503 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	chiral sulfinyl imines functionalized organolithium compounds diastereoselective additions piperidine alkaloids isosolenopsin A Organic chemistry QD241-441
spellingShingle	chiral sulfinyl imines functionalized organolithium compounds diastereoselective additions piperidine alkaloids isosolenopsin A Organic chemistry QD241-441 Ana Sirvent Francisco Foubelo Miguel Yus Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
description	The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to <i>N</i>-<i>tert</i>-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.
format	article
author	Ana Sirvent Francisco Foubelo Miguel Yus
author_facet	Ana Sirvent Francisco Foubelo Miguel Yus
author_sort	Ana Sirvent
title	Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
title_short	Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
title_full	Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
title_fullStr	Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
title_full_unstemmed	Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
title_sort	stereoselective synthesis of δ- and ε-amino ketone derivatives from <i>n</i>-<i>tert</i>-butanesulfinyl aldimines and functionalized organolithium compounds
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/1abb41bfe87547e09a65eb82a15fb954
work_keys_str_mv	AT anasirvent stereoselectivesynthesisofdandeaminoketonederivativesfrominiitertibutanesulfinylaldiminesandfunctionalizedorganolithiumcompounds AT franciscofoubelo stereoselectivesynthesisofdandeaminoketonederivativesfrominiitertibutanesulfinylaldiminesandfunctionalizedorganolithiumcompounds AT miguelyus stereoselectivesynthesisofdandeaminoketonederivativesfrominiitertibutanesulfinylaldiminesandfunctionalizedorganolithiumcompounds
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Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds

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