ChemInform Abstract: Facile Preparation of Novel Nonracemic Oxy-Substituted Cyclopropanone S,S-Acetals by γ-Cyclization of Glyceric Aldehyde Dithioacetal Derivatives and Studies of Their Reactivity.
✍ Scribed by H.-G. SCHWARZ; S. DREESSEN; A. TERSAKIAN; E. SCHAUMANN
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Facile Preparation of Novel Nonracemic Oxy-Substituted Cyclopropanone S,S-Acetals by γ-Cyclization of Glyceric Aldehyde Dithioacetal Derivatives and Studies of Their Reactivity.
-Glyceric aldehyde dithioacetals are useful three-carbon precursors for the production of desired cyclopropane derivatives. Thus, γ-cyclization of the chiral compounds (II) via their tosylates in the presence of electrophiles yields the title compounds (VI). Chromatographic purification of (VIa) provides the unstable spiro alcohol (VII) which on treatment with Burgess' reagent gives the unusual etherification product (VIII) with retention of configuration. -