Concepedia

Chiral organometallic reagents, IV. Stereoselective formation of β‐silyloxy‐α‐bromoalkyllithium compounds

Reinhard W. Hoffmann, Manfred Julius

Liebigs Annalen der Chemie · 1991 · 19 citations · 21 references

DOI

Concepts

Abstract

Abstract The diastereomeric carbenoids 4 have been generated by diastereoselective (84:16) exchange of the diastereotopic bromine atoms in the dibromo compound 3 for lithium at −120°C. The implication of the observed diastereoselectivity for the Nozaki ring‐expansion method is discussed.

References

21

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Akihiro Abe, Robert L. Jernigan, Paul J. Flory · Journal of the American Chemical Society · 1966 · 425 citations

, , +8

The Unambiguous Specification of the Steric Course of Asymmetric Syntheses

Dieter Seebàch, V. Prelog · Angewandte Chemie International Edition in English · 1982 · 362 citations

, , +11

Rotational barriers. 2. Energies of alkane rotamers. An examination of gauche interactions

Kenneth B. Wiberg, Mark A. Murcko · Journal of the American Chemical Society · 1988 · 156 citations

, , +11

Synthetically useful .beta.-lithioalkoxides from reductive lithiation of epoxides by aromatic radical anions

Theodore Cohen, In Howa Jeong, Boguslaw Mudryk et al. · The Journal of Organic Chemistry · 1990 · 103 citations

, , +5

Synthesis of 1,3-diol synthons from epoxy aromatic precursors: an approach to the construction of polyacetate-derived natural products

David A. Evans, Joelle A. Gauchet-Prunet, Erick M. Carreira et al. · The Journal of Organic Chemistry · 1991 · 91 citations

, , +5