Vicinal epoxymesylates: substrates for iterative organocuprate Chemistry

Mark J. Kurth, Melwyn A. Abreo

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Reacting vicinal epoxymesylates of general structure i with higher order and mixed higher order organocuprate reagents is shown to be very selective for attack at the least hindered epoxide center. The iterative application of this reaction - a sequence which consists of cuprate opening of epoxide i, reformation of an epoxide (I→ii), and subsequent cuprate opening of this intermediate epoxide (ii→iii) - provides ready access to acyclic carbon frameworks with up to three contiguous stereogenic centers.

Original languageEnglish (US)
Pages (from-to)5085-5092
Number of pages8
JournalTetrahedron
Volume46
Issue number15
DOIs
StatePublished - 1990

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Epoxy Compounds
Substrates
Carbon

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Vicinal epoxymesylates : substrates for iterative organocuprate Chemistry. / Kurth, Mark J.; Abreo, Melwyn A.

In: Tetrahedron, Vol. 46, No. 15, 1990, p. 5085-5092.

Research output: Contribution to journalArticle

Kurth, Mark J. ; Abreo, Melwyn A. / Vicinal epoxymesylates : substrates for iterative organocuprate Chemistry. In: Tetrahedron. 1990 ; Vol. 46, No. 15. pp. 5085-5092.
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