X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate

Barr, D. A.; Dorrity, M. J. R.; Grigg, Ronald; Hargreaves, S.; Malone, John F.; Montgomery, John; Redpath, James; Stevenson, Paul J.; Thornton‐Pett, Mark

doi:10.1016/0040-4020(94)00940-v

Cited by 57 publications

(31 citation statements)

References 50 publications

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“…34 Chiral azomethine ylides (both cyclic and acyclic), [186][187][188][189][190] chiral dipolarophiles [191][192][193] and chiral catalysts 74,191 have all been successfully implemented for asymmetric induction in azomethine ylide 1,3-dipolar cycloadditions.…”

Section: Asymmetric 13-dipolar Cycloadditions Of Azomethine Ylidesmentioning

confidence: 99%

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Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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Section: Asymmetric 13-dipolar Cycloadditions Of Azomethine Ylidesmentioning

confidence: 99%

“…192,194,195 However, excellent results have also been achieved with chiral acrylamides, and the synthesis of a number of biologically active compounds has been accomplished through their use.…”

Section: Asymmetric 13-dipolar Cycloadditions Of Azomethine Ylidesmentioning

confidence: 99%

Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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“…Thus the substituted pyrrolidines (3a-c) were prepared from the corresponding imines (2a-c)12 ' 19 in 85-94% yield as autlined in scheme 1. The reaction of these pyrolidine cycloadducts (3a-c) with henzoylisothiocyanate in acetonitrile at ambient temperature for 3-4 h gave henzoylaminocarbothioyl pyrrolidine (4a-c) in 90-98% yield (Scheme 1).…”

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confidence: 99%

“…An example of chiral version of henzoylaminocarbothioyl pyrrolidine derivative was also reported. This was prepared from chiral pyrrolidine (3d) oryginated from menthyl acrylate as dipolarophile via cycloaddition cascade pocesses 12,19. The cycloadduct was then treated with henzoylisothiocyanate under similar conditions (MeCN, rt, 4h) to afford chiral henzoylaminocarbothioyl pyrrolidine (4d) in 92% yield as a 3:1 rotomer (scheme 1).…”

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confidence: 99%

Novel Highly Functionalized Benzoylaminocarbothioyl Pyrrolidine from Benzoylisothiocyanate and Substitueted Pyrrolidine Derived From α-Aminoasit Ester via Imine -Azomethine Ylide- 1,3-Dipolar Cycloaddition Cascade

Döndaş¹,

Altinbas²

2004

Heterocyclic Communications

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A series of novel highly functionalized benzoylaminocarbothioyl pyrrolidines were prepared by the reaction of benzoylisothiocyanate with substitueted pyrrolidine derived from α -aminoasit ester via metal catalsed imine -azomethine ylides-l,3-Dipolar Cycloaddition in excellent yield. An example of chiral version benzoylaminocarbothioyl pyrrolidine were also reported. The chirality oryginated from menthyl acrylate as chiral dipolarophile in the cycloaddition cascade and induced three novell chiral centres.Introduction:

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“…The beneficial effect of silver salts as catalysts in 1,3-DCs is well documented. [22][23] In certain cases under conditions B, only the syn diastereomer was formed. The presence of AgNO 3 plays a vital role in the formation of cycloadduct from substrate 1j, which was unproductive under thermal conditions A.…”

Section: Introductionmentioning

confidence: 99%