A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions |
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Authors: | Sarakinos G Corey E J |
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Affiliation: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. |
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Abstract: | [formula: see text] The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure. The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55 degrees C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+)- or (-)-2. Esters of (+)- and (-)-2 can be converted to Z-potassium enolates and alkylated with high face selectivity. |
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