Concepedia

Guanidine-catalyzed Asymmetric Addition Reactions: Michael Reaction of Cyclopentenone with Dibenzyl Malonates and Epoxidation of Chalcone

Tsutomu Ishikawa, Takuya Kumamoto, Keiko Ebine, Miyuki Endo, Yukari Araki, Yuji Fushimi, Ikue Miyamoto, Toshio Isobe, Keiko Fukuda

Heterocycles · 2005 · 26 citations · 25 references

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Abstract

Several kinds of modified guanidines designed by us were applied to two types of asymmetric synthesis as superbases: Michael reactions of cyclopentenone with dibenzyl malonates and epoxidation of chalcone.Good to moderate asymmetric inductions were observed in these guanidine-catalyzed reactions.

References

25

Catalytic asymmetric synthesis

Choice Reviews Online · 2001 · 2.7K citations

, , +17

“Synthetic Enzymes”. Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene‐Water‐Poly[(S)‐alanine] System

S. JULIA, Jaume Masana, J. C. Vega · Angewandte Chemie International Edition in English · 1980 · 352 citations

, , +1

Catalytic Asymmetric Epoxidation of α,β-Unsaturated Ketones Promoted by Lanthanoid Complexes

Masahiro Bougauchi, Shizue Watanabe, Takayoshi Arai et al. · Journal of the American Chemical Society · 1997 · 286 citations

, , +13

Mechanism and Conditions for Highly Enantioselective Epoxidation of α,β-Enones Using Charge-Accelerated Catalysis by a Rigid Quaternary Ammonium Salt

E. J. Corey, Fuyao Zhang · Organic Letters · 1999 · 226 citations

, , +11

Superior amine catalysts for the Baylis–Hillman reaction: the use of DBU and its implications†

Varinder K. Aggarwal, Andrea Mereu · Chemical Communications · 1999 · 224 citations

, , +13