Further studies of intramolecular michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems

Praveen Kumar, Puhui Li, Ilia Korboukh, Tony L. Wang, Hemant Yennawar, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

A wide variety of stabilized carbanions have been found to participate as nucleophiles in intramolecular Michael-type conjugate additions to in situ generated nitrosoalkenes to form bridged carbocyclic systems. The vinylnitroso platforms for these cyclizations have been prepared via two key steps involving ring-closing metathesis of vinyl chlorides and regioselective conversion of vinyl chlorides to α-chloroketones with sodium hypochlorite in glacial acetic acid/acetone. An alternative approach to preparation of some cyclization substrates has involved use of more reactive enol ethers as precursors to the requisite α-chloroketones. A sulfonamide anion has also been found to be an effective nucleophile in this type of reaction, leading to formation of a 6-azabicyclo[3.2.1]octane.

Original languageEnglish (US)
Pages (from-to)2094-2101
Number of pages8
JournalJournal of Organic Chemistry
Volume76
Issue number7
DOIs
StatePublished - Apr 1 2011

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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