A highly enantioselective four-component reaction for the efficient construction of chiral β-hydroxy-α-amino acid derivatives.

@article{Qian2013AHE,
  title={A highly enantioselective four-component reaction for the efficient construction of chiral $\beta$-hydroxy-$\alpha$-amino acid derivatives.},
  author={Yu Qian and Changcheng Jing and Shunying Liu and Wenhao Hu},
  journal={Chemical communications},
  year={2013},
  volume={49 26},
  pages={
          2700-2
        }
}
An enantioselective four-component reaction of a diazoketone, water, an aniline and ethyl glyoxylate in the presence of catalytic Rh2(OAc)4 and a chiral Brønsted acid was developed to efficiently produce β-hydroxy-α-amino acid derivatives in good yields with high diastereoselectivity and enantioselectivity. 
32 Citations

A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines.

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated and the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

Efficient synthesis of chiral cyclic acetals by metal and Brønsted acid co-catalyzed enantioselective four-component cascade reactions.

Four-component Mannich reactions subsequently followed by an intramolecular oxo-Michael addition were developed to efficiently produce chiral cyclic acetals with high diastereoselectivity and

Enantioselective oxidative functionalization of the Csp3-H bond adjacent to a nitrogen atom for rapid access to β-hydroxyl-α-amino acid derivatives.

The method provided rapid access to a variety of highly functionalized β-hydroxyl-α-amino acid derivatives from simple starting materials under mild conditions.

Highly diastereoselective synthesis of 3-hydroxy-2,2,3-trisubstituted indolines via intramolecular trapping of ammonium ylides with ketones.

A series of 3-hydroxy-2,2,3-trisubstituted indolines are produced in good yields with excellent diastereoselectivities via an intramolecular aldol-type trapping of ammonium ylides with ketone units.

A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides.

A novel tandem intermolecular ammonium ylide formation/intramolecular Mannich-type [5+1] cyclization reaction of aryl diazoacetates and ortho-aminophenyl imine derivatives was developed. The reaction

Synergistic Rhodium/Phosphoric Acid Catalysis for the Enantioselective Addition of Oxonium Ylides to ortho-Quinone Methides.

We report herein a powerful and highly stereoselective protocol for the domino-type reaction of diazoesters with ortho-quinone methides generated in situ to furnish densely functionalized chromans

A visible-light photoredox-catalyzed four-component reaction for the construction of sulfone-containing quinoxalin-2(1H)-ones

A visible-light photoredox-catalyzed four component reaction of quinoxalin-2(1H)-ones, alkenes, aryldiazonium, and sodium metabisulfite leading to sulfone-containing quinoxalin-2(1H)-ones has been

Recent advances in the chemistry of Rh carbenoids: multicomponent reactions of diazocarbonyl compounds

Multicomponent reactions of diazo compounds catalyzed by complexes become a powerful tool for organic synthesis. They enable three- or four-step processes to be carried out as one-pot procedures

References

SHOWING 1-10 OF 50 REFERENCES

Cooperative catalysis in highly enantioselective Mannich-type three-component reaction of a diazoacetophenone with an alcohol and an imine.

A highly enantioselective three-component reaction of a diazoacetophenone, an alcohol, and an imine catalyzed cooperatively by Rh(2)(OAc)(4) and BINOL-derived chiral phosphoric acid has been

Selectivity control in enantioselective four-component reactions of aryl diazoacetates with alcohols, aldehydes and amines: an efficient approach to synthesizing chiral beta-amino-alpha-hydroxyesters.

Enantioselective four-component reactions of aryl diazoacetates with alcohols, aldehydes and amines catalyzed cooperatively by a rhodium complex and a chiral Brønsted acid produce

Cooperative catalysis with chiral Brønsted acid-Rh2(OAc)4: highly enantioselective three-component reactions of diazo compounds with alcohols and imines.

An asymmetric three-component reaction of diazo compounds and alcohols with imines catalyzed cooperatively by a rhodium complex and a chiral Brønsted acid provides a general and efficient entry to

A highly diastereoselective three-component tandem 1,4-conjugated addition-cyclization reaction to multisubstituted pyrrolidines.

A highly diastereoselective three-component tandem 1,4-conjugate addition-cyclization reaction of diazoacetophenones with anilines and unsaturated ketoesters was developed. The reaction provides

One-pot three-component tandem reaction of diazo compounds with anilines and unsaturated ketoesters: a novel synthesis of 2,3-dihydropyrrole derivatives.

A facile synthesis of 2,3-dihydropyrrole derivatives has been achieved through the one-pot, three-component tandem reaction of diazo compounds with anilines and beta,gamma-unsaturated

Asymmetric synthesis of beta-hydroxy amino acids via aldol reactions catalyzed by chiral ammonium salts.

These results represent the highest ee's obtained to date in direct aldol reactions of glycine equivalents catalyzed by inexpensive, readily prepared chiral ammonium salts.

Direct-type aldol reactions of fluorenylidene-protected/activated glycine esters with aldehydes for the synthesis of β-hydroxy-α-amino acid derivatives.

Aldol reaction of glycine Schiff base (I) with various aliphatic aldehydes provides the desired aldol products with high diastereoselectivities.

The direct catalytic asymmetric aldol reaction.

This critical review documents the development of direct catalytic asymmetric aldol methodologies, including organocatalytic and metal-based strategies, which have improved the reactivity, selectivity and substrate scope of the direct a Aldol reaction and enabled the synthesis of complex molecular targets.

Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines and functions as an excellent catalyst.

Diastereoselectively switchable enantioselective trapping of carbamate ammonium ylides with imines.

The intriguing Rh(2)(OAc)(4) and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α-substituted α,β-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.