Concepedia

Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

Emeline Vedrenne, Olov Wallner, Maxime R. Vitale, Frank Schmidt, Varinder K. Aggarwal

Organic Letters · 2008 · 77 citations · 34 references

DOI

Abstract

Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

References

34

Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis

Makoto Tokunaga, Jay F. Larrow, Fumitoshi Kakiuchi et al. · Science · 1997 · 1.4K citations

Lithiated Carbamates: Chiral Carbenoids for Iterative Homologation of Boranes and Boronic Esters

Jake L. Stymiest, Guillaume Dutheuil, Varinder K. Aggarwal · Angewandte Chemie International Edition · 2007 · 249 citations

, , +16

(Chloromethyl)lithium: efficient generation and capture by boronic esters and a simple preparation of diisopropyl (chloromethyl)boronate

K. M. SADHU, Donald S. Matteson · Organometallics · 1985 · 247 citations

, , +12

Iterative Stereospecific Reagent-Controlled Homologation of Pinacol Boronates by Enantioenriched α-Chloroalkyllithium Reagents

Paul R. Blakemore, Matthew S. Burge · Journal of the American Chemical Society · 2007 · 147 citations

, , +12

Asymmetric Synthesis of α‐Substituted Allyl Boranes and Their Application in the Synthesis of Iso‐agatharesinol

Guang Yu Fang, Varinder K. Aggarwal · Angewandte Chemie International Edition · 2006 · 115 citations

, , +13