Weak Arene CH⋅⋅⋅O Hydrogen Bonding in Palladium‐Catalyzed Arylation and Vinylation of Lactones

Huang, Zhiyan; Chen, Zuliang; Lim, Li Hui; Quang, Gia Chuong Phan; Hirao, Hajime; Zhou, Jianrong Steve

doi:10.1002/anie.201300481

Cited by 89 publications

(59 citation statements)

References 73 publications

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“…9). 26,27 The increased anti -selectivity using toluene over THF as the primary solvent (Table 3, entries 1/8 vs. 2/9) agreed with this hypothesis, as electrostatic interactions should be accentuated in nonpolar media. Although a reversal of selectivity was observed with the 8-fluorinated derivative (Table 5, entry 16), this was a lone case, and the unusual results with the 8-methyl derivative (Table 5, entries 12-15) render this hypothesis speculative at best.…”

Section: Resultssupporting

confidence: 62%

An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

2015

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Alkylations of proline-based imidazolidinones are described based on the principle of self-regeneration of stereocenters (SRS), affording high levels of either the cis or trans configured products. Stereoselectivity is dictated solely on the nature of the “temporary” group, where isobutyraldehyde-derived imidazolidinones provide the cis configured products and 1-naphthaldehyde-derived imidazolidinones afford the complementary trans configured products. These stereodivergent products can be readily cleaved to afford both α-alkylated proline enantiomers from readily available L-proline. A series of imidazolidinones were alkylated to investigate the origin of the anti-selectivity. Potential contributions toward the observed anti-selectivity are discussed on the basis of these experiments, suggesting a refined hypothesis for selectivity may be in order.

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Section: Resultssupporting

confidence: 62%

An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

2015

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“…[30] This kind of attractive interaction was absent in TS-R. Recently,t he use of aryl CH···O hydrogen bonding and other weak attractive forces have emerged in asymmetric metal catalysis. [31] In summary,wereport areductive Heck reaction process which uses aryl halides directly to afford 3-arylindanones in high ee values.Asakey reaction design, alkylammonium salts and glycol were used as hydrogen-bond donors to help halide dissociation under mild reaction conditions.Alkylammonium salts are routinely formed from alkylamines in asymmetric Heck reactions [32] and they may act as halide abstractors in polar solvents in, for example,O vermans Heck cyclizations. [33] Scheme 2.…”

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confidence: 99%

Palladium‐Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides

et al. 2015

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“…There is a CH··O/S intramolecular HB that influences the conformation of Meldrum's acid derivatives, a bond that persists in the gas phase [137]. CH··O HBs can control the stereochemistry during palladium-catalyzed arylation and vinylation of lactones [217,218]. They are part of the mechanism by which aminophosphonate diesters adopt their equilibrium structures [219].…”

Section: Fluoroamidesmentioning

confidence: 98%

The CH‥O H-Bond as a Determining Factor in Molecular Structure

Scheiner

2015

Challenges and Advances in Computational Chemistry and Physics

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The factors that affect the strength of CH··O hydrogen bonds (HBs) are enumerated, along with the source of their stability, and the structural and spectroscopic features that signal their presence. Their influence upon a number of chemical and biological processes is discussed. Within the context of proteins, the C α H group of protein residues can engage in CH··O HBs, as can the CH groups of a number of amino acid side chains including aromatic residues. CH··O HBs have the potential to make a major contribution to protein folding, particularly in an aqueous environment. These unconventional HBs may play as important a role in the formation of protein β-sheet structures as do NH··O HBs. The strength of CH··O HBs is magnified several-fold by the presence of positive charge on the proton donor. The implications of these principles are discussed for a number of specific biological and chemical problems, which include the catalytic mechanisms of methyltransferases and serine proteases, and the structural properties of fluoroamides.

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Weak Arene CH⋅⋅⋅O Hydrogen Bonding in Palladium‐Catalyzed Arylation and Vinylation of Lactones

Cited by 89 publications

References 73 publications

An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

Palladium‐Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides

The CH‥O H-Bond as a Determining Factor in Molecular Structure

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