Concepedia

Mono thiomalonates as thioester enolate equivalents—enantioselective 1,4-addition reactions to nitroolefins under mild conditions

Paolo Clerici, Helma Wennemers

Organic & Biomolecular Chemistry · 2011 · 37 citations · 33 references

DOI

Concepts

Abstract

Mono thiomalonates (MTMs) are introduced as thioester enolate equivalents. Asymmetric organocatalyzed conjugate addition reactions to nitroolefins proceed under mild conditions to afford synthetically useful γ-nitrothioesters with excellent yields and enantioselectivities.

References

33

Equilibrium acidities in dimethyl sulfoxide solution

F. G. Bordwell · Accounts of Chemical Research · 1988 · 2.8K citations

, , +7

Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts

Tomotaka Okino, Yasutaka Hoashi, Yoshiji Takemoto · Journal of the American Chemical Society · 2003 · 1.4K citations

, , +4

Highly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts

Benedek Vakulya, Szilárd Varga, Tibor Soós · Organic Letters · 2005 · 979 citations

, , +7

Highly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts.

Benedek Vakulya, Szilárd Varga, Antal Csámpai et al. · ChemInform · 2005 · 816 citations · Full text

, , +9

Urea‐ and Thiourea‐Substituted Cinchona Alkaloid Derivatives as Highly Efficient Bifunctional Organocatalysts for the Asymmetric Addition of Malonate to Nitroalkenes: Inversion of Configuration at C9 Dramatically Improves Catalyst Performance.

Séamus H. McCooey, Stephen J. Connon · Angewandte Chemie International Edition · 2005 · 660 citations

, , +8