C. Chiappe, G. Moro, Paola Munforte
Jul 1, 1997
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Naphthyl 3,4,6- tri -O- methyl-β- d -glucopyranoside , easily synthesized from tri -O- acetyl- d -glucal , has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6- tetra -O- methyl-β- d -glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and π-stacking effects, is proposed on the basis of the observed results.