Concepedia

Catalytic Regiodivergent Kinetic Resolution of Allylic Epoxides:  A New Entry to Allylic and Homoallylic Alcohols with High Optical Purity

Mauro Pineschi, Federica Del Moro, Paolo Crotti, Valeria Di Bussolo, Franco Macchia

The Journal of Organic Chemistry · 2004 · 46 citations · 26 references

DOI

Concepts

Abstract

A novel regiodivergent kinetic resolution of a series of allylic epoxides with alkylzinc reagents is described. Results demonstrate the potential of chiral copper-phosphoramidite catalysts for enantiomer differentiation of allylic epoxides, allowing a chiral catalyst-stereoregulated synthesis of cyclic allylic and homoallylic alcohols with high optical purities.

References

26

Highly Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc Reagents

B.L. Feringa, Mauro Pineschi, Leggy A. Arnold et al. · Angewandte Chemie International Edition in English · 1997 · 448 citations · Full text

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Parallel Kinetic Resolution

Edwin Vedējs, Xinhai Chen · Journal of the American Chemical Society · 1997 · 223 citations

, , +6

Platinum-Catalyzed Oxidations with Hydrogen Peroxide: Enantiospecific Baeyer-Villiger Oxidation of Cyclic Ketones

Andrea Gusso, Carla Baccin, Francesco Pinna et al. · Organometallics · 1994 · 162 citations

, , +13

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

Microbiological transformations. 22. Microbiologically mediated Baeyer-Villiger reactions: a unique route to several bicyclic .gamma.-lactones in high enantiomeric purity

Véronique Alphand, Roland Furstoss · The Journal of Organic Chemistry · 1992 · 147 citations

, , +6