Concepedia

Enantioselective α-hydrogen-atom abstraction from an ester by an optically active amine-boryl radical

Pearl L. H. Mok, Brian P. Roberts

Journal of the Chemical Society Chemical Communications · 1991 · 19 citations · 11 references

DOI

Concepts

Abstract

The optically active amine-boryl radical IpcḂH â†� NMe2CH2CH2NMe2→ BH2Ipc (Ipc = isophinocampheyl)abstracts hydrogen enantioselectively from the α-C–H group of methyl 2-phenylpropanoate; partial kinetic resolution of the ester has been achieved in a catalytic manner.

References

11

Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity?

Victor S. Martı́n, Scott S. Woodard, Tsutomu Katsuki et al. · Journal of the American Chemical Society · 1981 · 774 citations

, , +8

Simple synthesis of monoisopinocampheylborane of high optical purity

Herbert C. Brown, John R. Schwier, Bakthan Singaram · The Journal of Organic Chemistry · 1978 · 60 citations

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Homolytic reactions of ligated boranes. Part 15. Comparative studies of amine–boranes as donor polarity reversal catalysts for hydrogen-atom abstraction

Parveen Kaushal, Pearl L. H. Mok, Brian P. Roberts · Journal of the Chemical Society Perkin Transactions 2 · 1990 · 56 citations

, , +12

Homolytic reactions of ligated boranes. Part 8. Electron spin resonance studies of radicals derived from ligated alkylboranes

Vikram Paul, Brian P. Roberts · Journal of the Chemical Society Perkin Transactions 2 · 1988 · 55 citations

, , +14

Polarity reversal catalysis of hydrogen atom abstraction reactions

Vikram Paul, Brian P. Roberts · Journal of the Chemical Society Chemical Communications · 1987 · 46 citations

, , +10