The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 2913-2923
- https://doi.org/10.1039/p19930002913
Abstract
Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph2PO) group, is regiospecific (acetate moves away from the Ph2PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.Keywords
This publication has 25 references indexed in Scilit:
- Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bondTetrahedron Letters, 1993
- Stereocontrolled synthesis of R or S E or Z unsaturated α—amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxidesTetrahedron Letters, 1993
- A new method for stereoselective homoallylic amine synthesisJournal of the Chemical Society, Perkin Transactions 1, 1993
- Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolinesTetrahedron Letters, 1991
- The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reactionJournal of the Chemical Society, Perkin Transactions 1, 1991
- Chiral synthesis of Z-2-butylidenecyclohexan-1-OL and -1-YL phenylsulphide from optically active phosphine oxidesTetrahedron Letters, 1990
- Extension of the horner-wittig reaction to the synthesis ofTetrahedron Letters, 1989
- Stereocontrolled (Tetrahedron Letters, 1985
- Transposition of allylic alcohols controlled by the Ph2PO group: Reagents for α-hydroxy-diene synthesis by the horner-wittig reactionTetrahedron Letters, 1985
- Synthesis of the cytochalasin D isoindolone unit: solutions to the problem of regiochemistry in N-benzoylpyrrolinone Diels-Alder reactionsThe Journal of Organic Chemistry, 1982