Abstract
We show a convenient decarboxylative aldol process using a scandium catalyst and a PYBOX ligand to generate a series of highly functionalized chiral α-hydroxy esters. The protocol tolerates a broad range of β-keto acids with inactivated aromatic and aliphatic α-keto esters. The possible mechanism is rationalized.
Highlights
The catalytic enantioselective construction of tertiary carbon centres is a major challenge in organic chemistry
We presume that relatively hindered α-keto esters could be engaged as aldehydes in the decarboxylative aldol reactions with β-keto acids, which would provide a practical and effi
PyBox ligands 4–8 (Table 1), we discovered that Sc(OTf)[3] and tridentate PyBox ligand 6a could promote the decarboxylative aldol reaction of β-keto acid 1a with α-keto ester 2a in excellent yield with high enantioselectivity in toluene
Summary
The catalytic enantioselective construction of tertiary carbon centres is a major challenge in organic chemistry. Other less reactive carbonyl derivatives such as isatins [11,12], ketimines [13] and sulfonylimines [14] have been employed with β-keto acids in the decarboxylative addition processes. Results and Discussion α-Keto esters as surrogates of aldehydes for the generation of chiral alcohols by stereocontrolled nucleophilic alkylation [1519], alkynylation [20,21], 1,2-addition [22-26] and aldol reaction [27-32] have been developed.
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