Stereocontrolled route to some optically active β-hydroxy phosphine oxides using the stereoselective addition of metallated phosphine oxides to proline-derived keto aminals
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 2117-2127
- https://doi.org/10.1039/p19960002117
Abstract
An asymmetric Horner–Wittig addition reaction with a chiral auxiliary attached to the electrophile is described. The key step is the addition of metallated phosphine oxides to Mukaiyama's proline-derived keto aminals (for which improved syntheses are described) and a detailed study of the factors affecting the stereoselectivity of these reactions is presented. In particular, by suitable choice of metallation conditions, complementary stereoselectivities are observed: reactions in THF with no additives are syn selective (Felkin non-chelation control) whereas reactions in toluene with added lithium bromide are anti selective (Cram chelation control).Keywords
This publication has 51 references indexed in Scilit:
- Stereocontrol in Organic Synthesis Using the Diphenylphosphoryl GroupAngewandte Chemie International Edition in English, 1996
- Asymmetric dihydroxylations of allylic phosphine oxidesTetrahedron Letters, 1995
- Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcoholsJournal of the Chemical Society, Perkin Transactions 1, 1995
- Catalytic Asymmetric DihydroxylationChemical Reviews, 1994
- Asymmetric epoxidation and kinetic resolution of allylic phosphine oxidesJournal of the Chemical Society, Perkin Transactions 1, 1994
- 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
- Chiral synthesis of Z-2-butylidenecyclohexan-1-OL and -1-YL phenylsulphide from optically active phosphine oxidesTetrahedron Letters, 1990
- The stereocontrolled Horner-Wittig reaction: synthesis of disubstituted alkenesJournal of the Chemical Society, Perkin Transactions 1, 1985
- Asymmetric syntheses based on 1,3-oxathianes. 2. Synthesis of chiral tertiary .alpha.-hydroxy aldehydes, .alpha.-hydroxy acids, glycols [R1R2C(OH)CH2OH], and carbinols [R1R2C(OH)Me] in high enantiomeric purity.Journal of the American Chemical Society, 1984