Concepedia

Stereochemical Control of Both C−C and C−N Axial Chirality in the Synthesis of Chiral <i>N</i>,<i>O-</i>Biaryls

Jossian Oppenheimer, Richard P. Hsung, Ruth Figueroa, Whitney L. Johnson

Organic Letters · 2007 · 106 citations · 30 references

DOI

Concepts

Abstract

A Rh(I)-catalyzed asymmetric [2 + 2 + 2] cycloaddition of achiral ynamides is described here. This work demonstrates a unique concept of stereochemical control of both the C-C and C-N axial chirality and provides an approach to the synthesis of chiral N,O-biaryls as well as chiral anilides.

References

30

Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines

Karl Anker Jørgensen · Angewandte Chemie International Edition · 2000 · 639 citations

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Recent advances in the chemistry of ynamines and ynamides

Craig A. Zificsak, Jason A. Mulder, Richard P. Hsung et al. · Tetrahedron · 2001 · 301 citations

, , +3

Enantioselective Synthesis of Axially Chiral Anilides through Rhodium-Catalyzed [2+2+2] Cycloaddition of 1,6-Diynes with Trimethylsilylynamides

Ken Tanaka, Kenzo Takeishi, Keiichi Noguchi · Journal of the American Chemical Society · 2006 · 242 citations

, , +8

A Highly Efficient and Flexible Synthesis of Substituted Carbazoles by Rhodium-Catalyzed Inter- and Intramolecular Alkyne Cyclotrimerizations

B. Witulski, C. Alayrac · Angewandte Chemie International Edition · 2002 · 212 citations

, , +9

Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and <i>Z</i>-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides

Yanshi Zhang, Richard P. Hsung, Jossian Oppenheimer et al. · The Journal of Organic Chemistry · 2006 · 204 citations

, , +12