Chemoenzymatic synthesis of ketomethylene tripeptide isosteres

Tao, Junhua; Hu, Shanghui; Tian, Qingping; Nayyar, N. K.; Babu, Srin

doi:10.1016/j.tetasy.2004.11.092

Cited by 3 publications

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…α-Amino ketones are widespread structural moieties, common to both natural and synthetic significant compounds in medicinal chemistry ( Figure 1) [1][2][3][4]. They are largely employed as building blocks in the preparation of a large number of molecules, in particular, 1,2-aminoalcohols, and vicinal diamines (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction

Albanese

Gaggero

2018

Catalysts

View full text Add to dashboard Cite

Abstract:The N-heterocyclic carbene(NHCs)-catalyzed aza-benzoin condensation reaction is an efficient, single step strategy which employs easily available substrates, such as aldehydes and imines, to provide α-amino ketones. The multifunctionality and high reactivity of α-amino ketones makes these structures attractive for medicinal chemistry and as precursors of a variety of amine derivatives. The different electrophilic characteristics of aldehydes and imines ensure a high regioselective reaction. Enantiomerically-enriched α-amino ketones have been synthesized through stereoselective couplings promoted by chiral N-heterocyclic carbenes. One-pot domino procedures, including an aza-benzoin step, allow valuable complex molecules to be accessed.

show abstract

Section: Introductionmentioning

confidence: 99%

An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction

Albanese

Gaggero

2018

Catalysts

View full text Add to dashboard Cite

show abstract

Stereoselective synthesis of GABOB, carnitine and statine phosphonates analogues

Ordóñez

Labastida-Galván

Lagunas‐Rivera

2010

Tetrahedron: Asymmetry

View full text Add to dashboard Cite

Organocatalytic Asymmetric Decarboxylative Amination of β-Keto Acids: Access to Optically Active α-Amino Ketones and 1,2-Amino Alcohols

Zhang

Zeng

et al. 2017

Org. Lett.

View full text Add to dashboard Cite

An organocatalytic asymmetric decarboxylative amination reaction of β-keto acids is described. Under mild reaction conditions, a series of chiral α-amino ketones were obtained in good to high yields (up to 99%) and enantioselectivities (up to 95% ee). A chiral 1,2-amino alcohol was synthesized from the corresponding decarboxylative amination product in several steps without loss of enantioselectivity.

show abstract

Chemoenzymatic synthesis of ketomethylene tripeptide isosteres

Cited by 3 publications

References 15 publications

An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction

An Overview on the N-Heterocyclic Carbene-Catalyzed Aza-Benzoin Condensation Reaction

Stereoselective synthesis of GABOB, carnitine and statine phosphonates analogues

Organocatalytic Asymmetric Decarboxylative Amination of β-Keto Acids: Access to Optically Active α-Amino Ketones and 1,2-Amino Alcohols

Contact Info

Product

Resources

About