The first example of regiospecific magnesium carbenoid 1,3-CH insertion: its mechanism and stereochemistry

Shingo Ogata, Shigeyuki Masaoka, Ken Sakai, Tsuyoshi Satoh

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Addition reaction of two geometrical isomers of 1-chlorovinyl p-tolyl sulfoxides, derived from unsymmetrical ketones and chloromethyl p-tolyl sulfoxide, with lithium enolate of tert-butyl acetate gave single isomers of the adduct, respectively. Treatment of each diastereomer with i-PrMgCl resulted in the formation of magnesium carbenoids. Highly regiospecific 1,3-CH insertion reaction was found to take place from the magnesium carbenoids to afford cyclopropanes in high yields. Stereochemistry of the adducts, reaction mechanism, and origin of the regiospecificity are discussed.

Original languageEnglish
Pages (from-to)5017-5021
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number29
DOIs
Publication statusPublished - Jul 16 2007

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Stereochemistry
sulfoxide
Isomers
Magnesium
Cyclopropanes
Sulfoxides
Addition reactions
Ketones
Lithium
tert-butyl acetate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The first example of regiospecific magnesium carbenoid 1,3-CH insertion : its mechanism and stereochemistry. / Ogata, Shingo; Masaoka, Shigeyuki; Sakai, Ken; Satoh, Tsuyoshi.

In: Tetrahedron Letters, Vol. 48, No. 29, 16.07.2007, p. 5017-5021.

Research output: Contribution to journalArticle

Ogata, Shingo ; Masaoka, Shigeyuki ; Sakai, Ken ; Satoh, Tsuyoshi. / The first example of regiospecific magnesium carbenoid 1,3-CH insertion : its mechanism and stereochemistry. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 29. pp. 5017-5021.
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