Michael reaction of ketones and β-nitrostyrenes catalyzed by camphor-10-sulfonamide-based prolinamide

Rani, Rashmi; Peddinti, Rama Krishna

doi:10.1016/j.tetasy.2010.09.012

Cited by 19 publications

(10 citation statements)

References 52 publications

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“…Those are mainly five‐ and six‐membered cyclic sulfonyl hydrazine derivatives prepared from camphor sulfonic acid 11–14. However, there are also more noncovalent camphor‐derived organocatalysts, the bulk of them comprised of pyrrolidinyl–camphor–derived bifunctional organocatalysts, where both camphor and pyrrolidine chiral frameworks, connected with an appropriate linker, act in synergy 15–24. All the above mentioned camphor‐derived organocatalysts have been prepared via derivatization of camphor i.e., camphorsulfonic acid at positions 2 and/or 10 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural elucidation of novel camphor‐derived thioureas

et al. 2012

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Nine novel (+)-camphor-derived thioureas have been prepared. 3-((Dimethylamino)methylene)camphor (2) served as the common precursor for the preparation of both, 2-thiourea 15-20 and 3-thiourea functionalized camphor derivatives 6, 7/7', respectively. Starting from 2, the latter were prepared in two or three steps whereas the former in five steps, respectively. Configuration of all novel compounds has been meticulously determined using NMR techniques and/or single crystal X-ray crystallography.

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Section: Introductionmentioning

confidence: 99%

Synthesis and structural elucidation of novel camphor‐derived thioureas

et al. 2012

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“…1). [27][28][29][30][31][32][33][34][35][36] To the best of our knowledge, we could not find any 3,5bis(trifluoromethyl)phenyl thiourea-derived bifunctional organocatalysts with camphor as the exclusive chiral framework. Considering camphor's vast potential for chemical manipulation and our previous experiences with monofunctional camphor-derived thioureas prompted us to investigate the possibility to prepare novel bifunctional thiourea camphor derivatives, preferably in a stereo-divergent synthesis.…”

Section: Introductionmentioning

confidence: 84%

“…Concerning the camphor‐derived noncovalent organocatalysts, the vast majority represent the pyrrolidinyl–camphor‐derived bifunctional organocatalysts, where both camphor and pyrrolidine chiral frameworks, connected with an appropriate linker, act in synergy (Fig. ) …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐(3‐(3,5‐bis(trifluoromethyl)phenyl)thioureido)‐3‐((dimethylamino)methyl)camphor organocatalysts

et al. 2012

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In a stereo-divergent synthesis, three novel camphor-derived bifunctional thiourea organocatalysts 7-9 have been prepared in five steps starting from (+)-camphor. In addition, borneol-derived bifunctional thiourea organocatalysts 19/19' have been prepared in three steps from (1S)-(+)-camphorquinone. Novel organocatalysts 7-9, 19/19' have been evaluated in a model reaction of Michael addition of dimethyl malonate to trans-β-nitrostyrene with low to moderate enantioselectivities (20%-60% ee). Configuration of all novel compounds has been meticulously determined using nuclear magnetic resonance (NMR) techniques.

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“…Rani and Peddinti reported camphor sulphonamide ( 179 a‐c ) (20 mol%) as organocatalysts for the asymmetric nitro Michael addition between β‐nitrostyrene 160 and cyclohexanone 11 in neat. The organocatalyst 179 a was found to be an efficient catalyst to afforded anti ‐Michael product in 90:10 dr with 61% ee of anti‐ Michael product 180 (Scheme ) …”

Section: Prolinamide Catalysed Direct Asymmetric Aldol Reactionmentioning

confidence: 99%

Prolinamide‐Catalysed Asymmetric Organic Transformations

2019

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Proline was reported as an enantioselective organocatalyst for direct asymmetric aldol reaction in the early 1971 s by two independent groups of researchers and the reaction was called the Hajos‐Parrish‐Eder‐ Sauer Wiechert reaction. The breakthrough of enantioselective organocatalysis was demonstrated by List and co‐workers in 2000 for intermolecular aldol reaction between benzaldehydes and ketone using proline as a catalyst. After this report many researchers were applied the proline as a catalyst for other organic transformation. The proline has a carboxylic functional group which can easily convert to the amide and known as prolinamide. Prolinamides were found to be a better catalyst compared to proline in the most of cases. In this review article we are compiling the results of the prolinamides catalyzed asymmetric organic transformation with insight of the mechanism of catalysis.

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Michael reaction of ketones and β-nitrostyrenes catalyzed by camphor-10-sulfonamide-based prolinamide

Cited by 19 publications

References 52 publications

Synthesis and structural elucidation of novel camphor‐derived thioureas

Synthesis and structural elucidation of novel camphor‐derived thioureas

Synthesis of 2‐(3‐(3,5‐bis(trifluoromethyl)phenyl)thioureido)‐3‐((dimethylamino)methyl)camphor organocatalysts

Prolinamide‐Catalysed Asymmetric Organic Transformations

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