Enantioselective synthesis of highly functionalised amides by copper-catalysed vinylogous Mukaiyama aldol reaction.

@article{Frings2010EnantioselectiveSO,
  title={Enantioselective synthesis of highly functionalised amides by copper-catalysed vinylogous Mukaiyama aldol reaction.},
  author={Marcus Frings and Daniel Goedert and Carsten Bolm},
  journal={Chemical communications},
  year={2010},
  volume={46 30},
  pages={
          5497-9
        }
}
Amides with quaternary stereogenic centers have been synthesised by catalytic asymmetric vinylogous Mukaiyama aldol reactions. The chiral copper-sulfoximine catalyst gives rise to products with moderate to good yields and up to 92% ee. 
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42 Citations

42 Citations

Enantioselective Synthesis of Highly Functionalized Amides by Copper-Catalyzed Vinylogous Mukaiyama Aldol Reaction.

The title reaction affords amides with quaternary stereogenic centers in moderate to good yields and with up to 92% e.e.

Direct enantioselective amination of α-ketoesters catalyzed by an axially chiral guanidine base.

The reaction produces enantioenriched multifunctionalized ketoesters which can be readily derivatized to β-amino-α-hydroxy esters with an aliphatic substituent at the β-position.

Asymmetric Copper-Catalyzed Vinylogous Mukaiyama Michael Addition of Cyclic Dienol Silanes to Unsaturated α-Keto Phosphonates.

A highly stereoselective vinylogous Mukaiyama Michael reaction (VMMR) leading to α-keto phosphonate-containing γ-butenolides with two stereogenic centers is described. The presented transformation is…

The Copper‐Catalyzed Oxidative N‐Acylation of Sulfoximines

An oxidative cross-coupling reaction between aldehydes and sulfoximines involving dual CH/NH functionalization has been developed and proceeds under mild reaction conditions to afford a series of valuable N-acylated sulf oximine derivatives in excellent yields.

Catalytic, asymmetric synthesis of phosphonic γ-(hydroxyalkyl)butenolides with contiguous quaternary and tertiary stereogenic centers.

A procedure that enables high yielding access to phosphonic γ-(hydroxyalkyl)butenolides with excellent regio-, diastereo- and enantiocontrol is reported. The simultaneous construction of up to two…

Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes.

Sulfoximinated sulfoxides were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.

Sulfoximinocarbonylation of aryl halides using heterogeneous Pd/C catalyst

A three component protocol has been developed for the synthesis of N-aroyl sulfoximines by the carbonylation of aryl halides followed by nucleophilic attack of NH-sulfoximines. This reaction…

Transition metal-free aroylation of NH-sulfoximines with methyl arenes.

A novel protocol towards N-aroylated sulfoximines from NH-sulfoximines and methyl arenes was herein demonstrated. The reaction took place in the presence of elemental iodine, requiring no external…

Copper-catalyzed oxidative cross-coupling of sulfoximines and alkynes.

This work considered oxidative cross-coupling methods for the construction of the respective C N bonds between two nucleophiles and found that this approach could also open access to N-alkynylated sulfoximines, an essentially unexplored substrate class.

Recent development of vinylogous Mukaiyama aldol reactions

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