Studies of intramolecular cyclizations of N-acyliminium ions derived from acyclic ketones

Unanticipated stereochemical and structural results

Wenchun Chao, Jacob H. Waldman, Steven M. Weinreb

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

(Matrix presented) Intramolecular cyclizations of a series of (E)- and (Z)-olefinic acyclic ketone-derived N-acyliminium ions have been studied. It has been found that both the course of the reaction and the stereochemistry of the products are critically dependent upon the tether length and olefin geometry of the cyclization substrate.

Original languageEnglish (US)
Pages (from-to)2915-2918
Number of pages4
JournalOrganic Letters
Volume5
Issue number16
DOIs
StatePublished - Aug 7 2003

Fingerprint

Cyclization
stereochemistry
Ketones
ketones
alkenes
Ions
Stereochemistry
Alkenes
products
matrices
geometry
ions
Geometry
Substrates

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Studies of intramolecular cyclizations of N-acyliminium ions derived from acyclic ketones : Unanticipated stereochemical and structural results. / Chao, Wenchun; Waldman, Jacob H.; Weinreb, Steven M.

In: Organic Letters, Vol. 5, No. 16, 07.08.2003, p. 2915-2918.

Research output: Contribution to journalArticle

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AU - Chao, Wenchun

AU - Waldman, Jacob H.

AU - Weinreb, Steven M.

PY - 2003/8/7

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