Continuum of mechanisms for nucleophilic substitutions of cyclic acetals.
The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.
Krumper
Jennifer R
JR
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Salamant
Walter A
WA
Woerpel
K A
KA
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008956:Models, Chemical; D015394:Molecular Structure; D055672:Static Electricity; D013237:Stereoisomerism
D000080:Acetals