Concepedia

Catalytic Enantioselective Indium-Mediated Allylation of Hydrazones

Gregory R. Cook, Robert B. Kargbo, Bikash C. Maity

Organic Letters · 2005 · 55 citations · 33 references

DOI

Concepts

Abstract

[reaction: see text] A facile and highly selective indium-mediated allylation of hydrazones utilizing BINOL ligands is described. Chiral (R)-3,3'-bistrifluoromethylBINOL afforded homoallylic amines in up to 97% ee with stoichiometric ligand. Employing only 10 mol % ligand afforded selectivity of up to 92% ee.

References

33

Catalytic Asymmetric Allylation of Imines via Chiral Bis-π-allylpalladium Complexes

Hiroyuki Nakamura, Kaori Nakamura, Yoshinori Yamamoto · Journal of the American Chemical Society · 1998 · 196 citations

, , +8

Indium-Mediated Organometallic Reactions in Aqueous Media:  The Nature of the Allylindium Intermediate

Tak Hang Chan, Yang Yang · Journal of the American Chemical Society · 1999 · 188 citations

, , +8

Chiral Sulfoxides as Neutral Coordinate-Organocatalysts in Asymmetric Allylation of <i>N</i>-Acylhydrazones Using Allyltrichlorosilanes

Shū Kobayashi, Chikako Ogawa, Hideyuki Konishi et al. · Journal of the American Chemical Society · 2003 · 186 citations

, , +6

Asymmetric Allylboration of Aldehydes and Ketones Using 3,3‘-Disubstitutedbinaphthol-Modified Boronates

T. Robert Wu, Lixin Shen, J. Michael Chong · Organic Letters · 2004 · 173 citations

, , +9

Stereospecific, Enantioselective Allylation of α‐Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral‐Coordinate Organocatalysts

Chikako Ogawa, Masaharu Sugiura, Shū Kobayashi · Angewandte Chemie International Edition · 2004 · 136 citations

, , +8