Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones

Gary H. Posner, Leah L. Frye, Martin Hulce

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Conjugate additions of many organometallic reagents to 2-(p-anisylsulfinyl)-2-cycloalkenones, 2 proceed with much greater diastereoselectivity than additions to the corresponding 2-(p-tolylsulfinyl)-2-cycloalkenones, 7. Complexation of 2 with zinc dibromide followed by addition of various Grignard reagents lead, after reductive removal of the sulfoxide, to 3-substituted cycloalkanones of higher optical purity than those obtained from 7. Addition of methyltitanium triisopropoxide to 2-(p-anisylsulfnyl)-2-cyclohexenone, 2b, in the absence of zinc dibromide, proceeds with virtually complete asymmetric induction.

Original languageEnglish
Pages (from-to)1401-1407
Number of pages7
JournalTetrahedron
Volume40
Issue number8
DOIs
StatePublished - 1984
Externally publishedYes

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sulfoxide
Zinc
Organometallics
Complexation
2-cyclohexen-1-one

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones. / Posner, Gary H.; Frye, Leah L.; Hulce, Martin.

In: Tetrahedron, Vol. 40, No. 8, 1984, p. 1401-1407.

Research output: Contribution to journalArticle

Posner, Gary H. ; Frye, Leah L. ; Hulce, Martin. / Asymmetric synthesis using enantiomerically pure 2-(p-anisylsulfinyl)-2-cycloalkenones. In: Tetrahedron. 1984 ; Vol. 40, No. 8. pp. 1401-1407.
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