Concepedia

Strong Bicyclic Guanidine Base-Promoted Wittig and Horner−Wadsworth−Emmons Reactions

Daniele Simoni, Marcello Rossi, Riccardo Rondanin, Angelica Mazzali, Riccardo Baruchello, Cinzia Malagutti, Marinella Roberti, Francesco Paolo Invidiata

Organic Letters · 2000 · 98 citations · 11 references

DOI

Concepts

Abstract

A convenient procedure to effect the Wittig and Horner-Wadsworth-Emmons reactions employs guanidine TBD and MTBD as base-promoters; mild reaction conditions, high efficiency, and facile isolation of the final products make the present methodology, at least in some cases, a practical alternative to known procedures.

References

11

Horner-wadsworth-emmons reaction: Use of lithium chloride and an amine for base-sensitive compounds

Mary A. Blanchette, William Choy, Jeffery T. Davis et al. · Tetrahedron Letters · 1984 · 910 citations

, , +1

Enantioselective Synthesis of α-Amino Nitriles from <i>N</i>-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as Catalyst

E. J. Corey, Michael J. Grogan · Organic Letters · 1999 · 468 citations

, , +14

Novel, Very Strong, Uncharged Auxiliary Bases; Design and Synthesis of Monomeric and Polymer‐Bound Triaminoiminophosphorane Bases of Broadly Varied Steric Demand

Reinhard Schwesinger, Jürgen Willaredt, Helmut Schlemper et al. · Chemische Berichte · 1994 · 248 citations

, , +12

1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems

Daniele Simoni, Riccardo Rondanin, Massimo Morini et al. · Tetrahedron Letters · 2000 · 126 citations

, , +8

Synthesis and properties of a series of sterically hindered guanidine bases

Derek H. R. Barton, John D. Elliott, Stephen D. Géro · Journal of the Chemical Society Perkin Transactions 1 · 1982 · 116 citations

, , +9