Concepedia

Dramatic Rate Enhancement of Asymmetric Phase‐Transfer‐Catalyzed Alkylations

Seiji Shirakawa, Kenichiro Yamamoto, Masanori Kitamura, Takashi Ooi, Keiji Maruoka

Angewandte Chemie International Edition · 2004 · 68 citations · 37 references

DOI

Concepts

Abstract

The intervention of crown ethers or achiral quaternary ammonium salts as achiral phase-transfer catalysts (PTCs, see scheme) in a chiral PTC system leads to dramatic rate enhancements in the asymmetric alkylation of glycine derivatives.

References

37

The Enantioselective Synthesis of α-Amino Acids by Phase-Transfer Catalysis with Achiral Schiff Base Esters

Martin O’Donnell · Accounts of Chemical Research · 2004 · 760 citations

, , +14

A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions

E. J. Corey, Feng Xu, Mark C. Noe · Journal of the American Chemical Society · 1997 · 669 citations

, , +8

Design and Synthesis of Metal Ion-Recognition-Induced Conjugated Polymers:  An Approach to Metal Ion Sensory Materials

Bing Wang, Michael R. Wasielewski · Journal of the American Chemical Society · 1997 · 559 citations

, , +16

Asymmetric Phase-Transfer Catalysis Utilizing Chiral Quaternary Ammonium Salts:  Asymmetric Alkylation of Glycine Imines

Barry Lygo, Benjamin I. Andrews · Accounts of Chemical Research · 2004 · 548 citations

, , +14

The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysis

Martin O’Donnell, William D. Bennett, Shengde Wu · Journal of the American Chemical Society · 1989 · 546 citations

, , +11