NDLI: Accessing N-Stereogenicity through a Double Aza-Michael Reaction: Mechanistic Insights

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Accessing N-Stereogenicity through a Double Aza-Michael Reaction: Mechanistic Insights

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Accessing N-Stereogenicity through a Double Aza-Michael Reaction: Mechanistic Insights

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kohrt, Sonja Cvengros, Ján Santschi, Nico
Description	Author Affiliation: Kohrt S ( Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich (Switzerland).); Santschi N ( Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany).); Cvengros J ( Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich (Switzerland).)
Abstract	Further development of the chemistry and applications of chiral compounds that possess configurationally stable stereogenic nitrogen atoms is hampered by the lack of efficient strategies to access such compounds in an enantiomerically pure form. Esters of propiolic acid and chiral alcohols were evaluated as cheap and readily available Michael acceptors in a diastereoselective synthesis of N-stereogenic compounds by means of a double aza-Michael conjugate addition. Diastereomeric ratios of up to 74:26 and high yields were achieved with (−)-menthyl propiolate as a substrate. Furthermore, a detailed mechanistic investigation was undertaken to shed some light on the course of this domino transformation. Kinetic studies revealed that the protic-solvent additive acts as a Brønsted acid and activates the ester toward the initial attack of the tetrahydrodiazocine partner. Conversely, acidic conditions proved unfavorable during the final cyclization step that provides the product.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	1
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-01-04
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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