Asymmetric hydrocyanation of hydrazones catalyzed by in situ formed O-silylated BINOL-phosphate: a convenient access to versatile alpha-hydrazino acids.

@article{Zamfir2010AsymmetricHO,
  title={Asymmetric hydrocyanation of hydrazones catalyzed by in situ formed O-silylated BINOL-phosphate: a convenient access to versatile alpha-hydrazino acids.},
  author={Alexandru Zamfir and Svetlana B. Tsogoeva},
  journal={Organic letters},
  year={2010},
  volume={12 1},
  pages={
          188-91
        }
}
A first organocatalytic enantioselective route was developed for the conversion of readily prepared and air stable aliphatic hydrazones to synthetically valuable alpha-hydrazinonitriles. This BINOL-phosphate catalyzed Strecker-type reaction (see scheme, Ar = p-NO(2)-Ph) provides a new practical and direct route to alpha-hydrazino acids of synthetic and biological importance. The actually active catalyst is proposed to be an in situ formed O-silylated BINOL-phosphate, thus shifting the nature of… Expand
35 Citations
Silicon Lewis Acid Catalyzed [3+2] Cycloaddition Reactions of Hydrazones/Cyclopentadiene: Mild Access to Pyrazolidine Derivatives
A first and fairly mild metal-free catalytic route was developed for the [3+2] cycloadditions of different N-acylhydrazones to cyclopentadiene, providing the synthetically andbiologically importantExpand
Lewis base catalyzed trialkylsilylcyanide additions to cyclic 2-fluoroketones: nucleophile directed access to both cis- and trans-stereoisomers
An efficient method for the Lewis base-catalyzed addition of trialkylorganosilanes (TMSCN & TBSCN) to cyclic 2-fluoroketones has been developed producing the TMS- or TBS-protected cyanohydrins inExpand
Asymmetric organocatalytic Strecker-type reactions of aliphatic N,N-dialkylhydrazones.
TLDR
The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented, yielding essentially pure enantiomers. Expand
Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides.
Catalysts generated by combinations of Pd(TFA)2 and pyridine-hydrazone ligands have allowed the asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protectedExpand
Chiral BINOL-derived phosphoric acids: privileged Brønsted acid organocatalysts for C-C bond formation reactions.
TLDR
The recent advances have been reviewed in this article with a focus being placed on hydrocyanations, aldol-type, Mannich, Friedel-Crafts, aza-ene- type, Diels-Alder, as well as cascade and multi-component reactions. Expand
Chiral Brønsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi-Sakurai Allylation Reactions.
TLDR
Highly diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Brønsted acid, N-(perfluorooctanesulfonyl)thiophosphoramide, is described, which allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of allylsilanes. Expand
Catalytic Asymmetric Cyanation Reactions
Catalytic asymmetric cyanations of prochiral unsaturated compounds affording the corresponding nitrile products in high enantiomeric excess (≥90% in general) are summarized in this review. TheExpand
Hydrocyanation of Unsaturated Imines Using Potassium Hexacyanoferrate(II) as a Cyanide Source
An efficient method for the hydrocyanation of unsaturated imines to synthesize β,γ-unsaturated α-aminonitriles by a one-pot two-step procedure using potassium hexacyanoferrate(II) as a cyanide sourceExpand
Hydrazones as Singular Reagents in Asymmetric Organocatalysis.
TLDR
The functional group transformations performed from the available products has been analyzed, highlighting the synthetic value of these methodologies, which served to access numerous families of valuable multifunctional compounds and nitrogen-containing heterocycles. Expand
Ruthenium-Catalyzed Enantioselective Hydrogenation of Hydrazones.
TLDR
The mild reaction conditions and broad functional group tolerance of this method allow access to versatile chiral hydrazine building blocks containing aryl bromide, heteroaryl, alkyl, cycloalkyl, and ester substituents. Expand
...
1
2
3
4
...