Concepedia

ASYMMETRIC [2,3]WITTIG SIGMATROPIC REARRANGEMENTS INVOLVING CHIRAL AMIDE ENOLATES AS THE MIGRATING TERMINI

Köichi Mikami, Osamu Takahashi, Takashi Kasuga, Takeshi Nakai

Chemistry Letters · 1985 · 28 citations · 7 references

DOI

Concepts

Abstract

Abstract The title rearrangement of the chiral (E-crotyloxy)acetamides derived from (S)-prolinol has been shown to provide a modest level of asymmetric induction (52–60%) along with a high erythro-selectivity (95–98%). The influence of the metal centers (Li, K, and Zr) and the ligating substituents on the prolinol part has been discussed.

References

7

Chiral enolate design

David A. Evans, James M. Takacs, Lawrence R. McGee et al. · Pure and Applied Chemistry · 1981 · 276 citations · Full text

, , +3

Enantioselective alkylation of chiral enolates

David A. Evans, James M. Takacs · Tetrahedron Letters · 1980 · 174 citations

, , +5

Enantioselective aldol condensations. 3. Erythro-selective condensations via zirconium enolates

David A. Evans, Lawrence R. McGee · Journal of the American Chemical Society · 1981 · 126 citations

, , +6

Asymmetric alkylation of carboxyamides by using trans-2,5-disubstituted pyrrolidines as chiral auxiliaries

Yasuhiro Kawanami, Yoshio Ito, Toshiyuki Kitagawa et al. · Tetrahedron Letters · 1984 · 123 citations

, , +7

Acyclic diastereoselection of the [2,3]-Wittig sigmatropic rearrangement of a series of isomeric crotyl ethers. A conceptual model for the transition-state geometry

Köichi Mikami, Yasunori Kimura, N. Kishi et al. · The Journal of Organic Chemistry · 1983 · 77 citations

, , +9