Chiral N-heterocyclic carbenes as asymmetric acylation catalysts

Suzuki, Yumiko; Muramatsu, Kazuyuki; Yamauchi, Kaori; Morie, Yasuko; Sato, Masayuki

doi:10.1016/j.tet.2005.09.071

Cited by 78 publications

(29 citation statements)

References 46 publications

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“…In 2004, Suzuki and co-workers reported the first examples of NHCs of type 23 (Scheme 15) as catalysts for enantioselective acyl transfers [122]. They applied them to the kinetic resolution of racemic secondary aryl alkyl alcohols [123]. Further examples were reported by Maruoka's group [124].…”

Section: N-heterocyclic Carbene-catalyzed Transesterificationsmentioning

confidence: 99%

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

et al. 2016

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Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organic chemistry. After reviewing the conceptual underpinnings of catalysis, we discuss the applications of different catalysts according to the mechanism of the reactions that they catalyze, including acyl group transfers, nucleophilic additions and substitutions, and C-C bond forming reactions that employ umpolung by nucleophilic additions to C=O and C=C double bonds. We highlight the utility of a broad range of organocatalysts other than compounds based on proline, the cinchona alkaloids and binaphthyls, which have been abundantly reviewed elsewhere. The focus is on organocatalysts, although a few examples employing metal complexes and enzymes are also included due to their significance. Classical Brønsted acids have evolved into electrophilic hands, the fingers of which are hydrogen donors (like enzymes) or other electrophilic moieties. Classical Lewis base catalysts have evolved into tridimensional, chiral nucleophiles that are N-(e.g., tertiary amines), P-(e.g., tertiary phosphines) and C-nucleophiles (e.g., N-heterocyclic carbenes). Many efficient organocatalysts bear electrophilic and nucleophilic moieties that interact simultaneously or not with both the electrophilic and nucleophilic reactants. A detailed understanding of the reaction mechanisms permits the design of better catalysts. Their construction represents a molecular science in itself, suggesting that sooner or later chemists will not only imitate Nature but be able to catalyze a much wider range of reactions with high chemo-, regio-, stereo-and enantioselectivity. Man-made organocatalysts are much smaller, cheaper and more stable than enzymes.

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Section: N-heterocyclic Carbene-catalyzed Transesterificationsmentioning

confidence: 99%

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

et al. 2016

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“…alcohols. 110 Suzuki et al proposed the following mechanism (Scheme 14). Selective acyl transfer mediated by NHCs seems to proceed via the same nucleophilic catalysis mechanism proposed for DMAP, DMAP-derivatives, N-alkyl imidazole-derivatives, amidines, amines, phosphines, and phosphinites (vide supra).…”

Section: Ohmentioning

confidence: 99%

6.08 Acylation-Type Reactions: Synthesis of Esters via Acyl Transfer

Zell

Schreiner

2014

Comprehensive Organic Synthesis II

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“…To our disappoint, replacing the Me group of L7 with an Et group decreased the enantioselectivity (entry 5). Introducing adamantyl (L9) 39 or mesityl (L10) 40 groups in place of the naphthyl substituents in L7 resulted in loss of enantiocontrol or complete inhibition of the reaction, respectively (entries 6 and 7). These results imply that introducing steric hindrance in close proximity to the α stereogenic center of N substituents is unfavorable.…”

Section: Conjugate Addition Of Alkylboranesmentioning

confidence: 99%

Copper-Catalyzed Allylic Substitution and Conjugate Addition with Alkylboranes

Ohmiya

Sawamura

2014

J. Synth. Org. Chem. Jpn.

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This account describes our studies on the use of alkylboranes for copper catalyzed allylic substitution and conjugate addition reactions. The wide availability of alkylboranes via the established alkene hydroboration reaction is an attractive feature of these transformations. Various functional groups are tolerated in the substrates. Catalytic mechanisms involving the formation of alkylcopper(I) species from alkylboranes through B/Cu transmetalation are proposed.

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Chiral N-heterocyclic carbenes as asymmetric acylation catalysts

Cited by 78 publications

References 46 publications

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

6.08 Acylation-Type Reactions: Synthesis of Esters via Acyl Transfer

Copper-Catalyzed Allylic Substitution and Conjugate Addition with Alkylboranes

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