Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides

Gary H. Posner, John P. Mallamo, Kyo Miura, Martin Hulce

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A new, general method is developed for preparation of various 3-substituted carbonyl compounds of very high optical purity. Application of this method is made to asymmetric synthesis of either enantiomer of 3-methylalkanoic acids, of optically pure 3-methylcyclopentanone, 3-methylcyclohexanone, 3-naphthylcyclopentanone 12 and 3-vinylcyclopentanone 14. 9,11-Seco steroid 12 and steroid intermediate 14 are precursors of optically pure steroidal equilenin and estrone of natural absolute configuration. The basis for this asymmetric synthetic method rests on the transfer of chirality from the sulfoxide sulfur atom to the 3-carbon carbon atom during organometallic 3-addition to optically pure α-carbonyl α.β-ethylenic sulfoxides.

Original languageEnglish
Pages (from-to)2307-2314
Number of pages8
JournalPure and Applied Chemistry
Volume53
Issue number12
DOIs
StatePublished - Jan 1 1981
Externally publishedYes

Fingerprint

Sulfoxides
sulfoxide
Organometallics
Equilenin
Carbon
Steroids
Carbonyl compounds
Atoms
Enantiomers
Estrone
Chirality
Sulfur
Acids
3-methylcyclopentanone

All Science Journal Classification (ASJC) codes

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides. / Posner, Gary H.; Mallamo, John P.; Miura, Kyo; Hulce, Martin.

In: Pure and Applied Chemistry, Vol. 53, No. 12, 01.01.1981, p. 2307-2314.

Research output: Contribution to journalArticle

Posner, Gary H. ; Mallamo, John P. ; Miura, Kyo ; Hulce, Martin. / Asymmetric synthesis using organometallic reagents and optically pure vinylic sulfoxides. In: Pure and Applied Chemistry. 1981 ; Vol. 53, No. 12. pp. 2307-2314.
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