The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

Levinger, S.; Nair, Ranjeet V.; Häßner, Alfred

doi:10.3762/bjoc.4.32

Cited by 4 publications

(4 citation statements)

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“…The conjugate addition of α-sulfonylallylic carbanions produced from 553 bearing a chiral auxiliary to an α,βunsaturated ester afforded the corresponding adducts 554 and 555 in good stereoselectivities. 400 In these reactions, a remote aromatic ring affects the stereochemical outcome. Among various aromatic substituents, the 9-anthryl group is the most effective and the reaction of 553c gave 99% de (Scheme 143a).…”

Section: Alkali Metal Cation-assisted Reactionsmentioning

confidence: 99%

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Cation−π Interactions in Organic Synthesis

2018

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The cation−π interaction is an attractive noncovalent interaction between a cation and a π system. Due to the stronger interaction energy than those of the other π interactions, such as π–π and CH−π interactions, the cation−π interaction has recently been recognized as a new tool for controlling the regio- and stereoselectivities in various types of organic reactions. This review attempts to cover a variety of organic reactions controlled by cation−π interactions, which includes not only recent examples but also those reported before the term “cation−π interaction” was defined in 1990. This review will provide comprehensive knowledge on the role of cation−π interactions in organic synthesis.

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Section: Alkali Metal Cation-assisted Reactionsmentioning

confidence: 99%

“…The conjugate addition of α-sulfonylallylic carbanions produced from 553 bearing a chiral auxiliary to an α,β -unsaturated ester afforded the corresponding adducts 554 and 555 in good stereoselectivities . In these reactions, a remote aromatic ring affects the stereochemical outcome.…”

Section: Metal Cation-assisted Reactionsmentioning

confidence: 99%

Cation−π Interactions in Organic Synthesis

2018

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“…For each t 1 value 16 scans were signal-averaged using a recycle delay of 2 s. HRMS and ESI (ESI+) mass spectra were recorded using an MicroToF Q, API-Q-ToF ESI with a mass range from 20 to 3000 m / z and mass resolution 15000 (fwhm). The synthesis of the ruthenium catalyst [Ru(p-cymene)(μ-Cl)Cl] 2 and amines 1b , 1c , 1d , 1e , 1f , 1g , 1i , and 1j have been carried out following published procedures. Other starting amines 1 and 6 and alkynes were purchased from commercial sources.…”

Section: Experimental Sectionmentioning

confidence: 99%

Primary Amines as Directing Groups in the Ru-Catalyzed Synthesis of Isoquinolines, Benzoisoquinolines, and Thienopyridines

2013

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Isoquinolines, benzoisoquinolines, thieno[3,2c]pyridines and fused heteroaryl[2,3-c] pyridines, with a wide variety of substituents at different positions of the aromatic or heteroaromatic rings, have been synthesized by Ru-catalyzed oxidative coupling of a broad range of benzylamines or heterocycles with internal alkynes. All benzylamines and heterocycles have unprotected primary amines as efficient directing groups.

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“…45 We finally checked the stability of the imine linker of 3, as imine bonds are known to be unstable in aqueous media or even in organic solvents containing traces of water, although their hydrolysis can be inhibited by steric hindrance. 46 The 1 H NMR analysis of 5 before and after three days of incubation in the serum shows no changes ( Fig. S6 and S7 †).…”

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confidence: 94%