Concepedia

Construction of Arene-Fused-Piperidine Motifs by Asymmetric Addition of 2-Trityloxymethylaryllithiums to Nitroalkenes:  The Asymmetric Synthesis of a Dopamine D1 Full Agonist, A-86929

Mitsuaki Yamashita, Ken‐ichi Yamada, Kiyoshi Tomioka

Journal of the American Chemical Society · 2004 · 59 citations · 13 references

DOI

Concepts

Abstract

The straightforward methodology for the construction of chiral arene-fused-piperidine motifs using a highly enantioselective addition of 2-trityloxymethylaryllithiums to cyclic and acyclic nitroalkenes has been developed. The versatility of the process was highlighted by the first asymmetric synthesis of a dopamine D1 full agonist, A-86929.

References

13

Dramatic Improvement of the Enantiomeric Excess in the Asymmetric Conjugate Addition Reaction Using New Experimental Conditions

A. Alexakis, Cyril Benhaïm, Stéphane Rosset et al. · Journal of the American Chemical Society · 2002 · 276 citations

, , +10

Hemilabile Amidomonophosphine Ligand−Rhodium(I) Complex-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Cycloalkenones

Masami Kuriyama, Kazushige Nagai, Ken‐ichi Yamada et al. · Journal of the American Chemical Society · 2002 · 167 citations

, , +14

Highly Enantioselective Conjugate Addition of Dialkylzinc Reagents to Acyclic Nitroalkenes:  A Catalytic Route to β<sup>2</sup>-Amino Acids, Aldehydes, and Alcohols

Ate Duursma, Adriaan J. Minnaard, Ben L. Feringa · Journal of the American Chemical Society · 2003 · 157 citations

, , +6

Novel strategy of using a C2 symmetric chiral diether in the enantioselective conjugate addition of an organolithium to an .alpha.,.beta.-unsaturated aldimine

Kiyoshi Tomioka, Mitsuru Shindo, Kenji Koga · Journal of the American Chemical Society · 1989 · 133 citations

, , +6

First Synthesis of a β<sup>2</sup>-Homoamino Acid by Enantioselective Catalysis

Audrius Rimkus, Norbert Sewald · Organic Letters · 2002 · 98 citations

, , +9