DISPIROKETALS IN SYNTHESIS .16. FUNCTIONALIZED DISPIROKETALS AS NEW CHIRAL AUXILIARIES - THE SYNTHESIS OF DIHYDROXYLATED DISPIROKETALS IN OPTICALLY PURE FORM AND THEIR APPLICATION AS BIFUNCTIONAL, C-2-SYMMETRICAL, CHIRAL AUXILIARIES FOR HIGHLY STEREOSELECTIVE MICHAEL ADDITIONS
Bcb. Bezuidenhoudt et al., DISPIROKETALS IN SYNTHESIS .16. FUNCTIONALIZED DISPIROKETALS AS NEW CHIRAL AUXILIARIES - THE SYNTHESIS OF DIHYDROXYLATED DISPIROKETALS IN OPTICALLY PURE FORM AND THEIR APPLICATION AS BIFUNCTIONAL, C-2-SYMMETRICAL, CHIRAL AUXILIARIES FOR HIGHLY STEREOSELECTIVE MICHAEL ADDITIONS, Recueil des travaux chimiques des Pays-Bas, 114(4-5), 1995, pp. 184-194
A range of rigid, architecturally complex diols derived from dispiroke
tals have been synthesised. A bifunctional, C-2-symmetrical, chiral au
xiliary derived from these dihydroxylated dispiroketals has been used
to induce a high degree of asymmetry in Michael additions of cuprates
to a variety of di-alpha,beta-unsaturated ester systems.