STEREOSELECTIVE ALDOL ADDITIONS TO α-ALKOXY ALDEHYDES USING THIOESTER SILYL KETENE ACETALS.
Relative stereochemistry (chelation) effectively controls internal stereochemistry (syn-anti) in the addition of thiopropionate equivalents to O-benzyl lactic aldehyde.
Gennari, Cesare,Bernardi, Anna,Poli, Giovanni,Scolastico, Carlo
LEWIS ACID MEDIATED ALDOL CONDENSATIONS USING THIOESTER SILYL KETENE ACETALS
BF3-OEt2 mediated thioester silylketene acetal additions to aldehydes are stereoconvergent and give high anti-syn ratios and good chemical yields.An acyclic transition state model was hypothesized in order to account for the observed selectivity.Theoretic
Gennari, Cesare,Beretta, M. Grazia,Bernardi, Anna,Moro, Giorgio,Scolastico, Carlo,Todeschini, Roberto
p. 893 - 910
(2007/10/02)
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