Asymmetric functionalisation of prochiral 1,3-diols based on an efficient 1,6-chiral induction: the diastereoselective C–O bond fission in chiral β-arylsulfinyl acetal via two types of chelation control
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 516-518
- https://doi.org/10.1039/c39920000516
Abstract
The novel asymmetric functionalisation of a prochiral 1,3-diol is accomplished by the diastereoselective C–O bond fission of the chiral β-arylsulfinyl acetal via two types of chelation controlled transition states (A and C in Scheme 4).This publication has 43 references indexed in Scilit:
- Organopalladium approaches to prostaglandins. 10. An efficient synthesis of prostaglandin E2 via vinylpalladation of 4-cyclopentene-1,3-diolTetrahedron Letters, 1989
- Acid-catalyzed rearrangement of pyran derivatives. An approach to the stereoselective synthesis of 1,3-diol derivativesTetrahedron Letters, 1989
- Methyl‐jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatürlichen Enantiomer via Palladium(0)‐induzierte, enantiodivergente Alkylierung von Cyclopent‐2‐en‐1,3‐diol‐DerivatenHelvetica Chimica Acta, 1989
- PALLADIUM(0)-CATALYZED syn-1,4-ADDITION OF CARBOXYLIC ACIDS TO CYCLOPENTADIENE MONOEPOXIDE: cis-3-ACETOXY-5-HYDROXYCYCLOPENT-1-ENEOrganic Syntheses, 1989
- A convenient procedure for the regioselective monoprotection of 1,n-diolsTetrahedron Letters, 1988
- Stereoselective Syntheses of Building Blocks with Three Consecutive Stereogenic Centers: Important Precursors of Polyketide Natural Products [New Synthetic Methods (68)]Angewandte Chemie International Edition in English, 1987
- Stereochemistry of the 1,2-Wittig rearrangement: A synthesis of syn-1,3-diol monoethersTetrahedron Letters, 1987
- Synthesis of 1,3-diol derivatives from sterically overcrowded oxiranes. Ring-opening reactions of 1-t-butyl-1,2-epoxycyclohexane.Journal of the Chemical Society, Perkin Transactions 1, 1985
- Oxymethylative opening of oxiranes leading to 1,3-diol derivatives by cobalt carbonyl catalyzed reaction with a hydrosilane and carbon monoxideJournal of the American Chemical Society, 1984
- Readily Available Chiral Carbon Fragments and Their Use in SynthesisPublished by Elsevier ,1984