Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl-and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents

RM Jacobson, GP Lahm, JW Clader

文献索引：Jacobson, Richard M.; Lahm, George P.; Clader, John W. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 395 - 405

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被引用次数: 1

摘要

The triniethylsilyl-(2) and ethoxyethyl-(4) protected cyanohydrins of a $-unsaturated aldehydes are utilized as three-carbon annelation reagents. Metalated reagent 2 displays exclusive a reactivity with aldehydes and ketones at-78" C. Metalated reagent 4 displays exclusive a reactivity at-78" C and exclusive y reactivity at 0" C. Reagent 4 thus allows for complete regiocontrol in its addition to aldehydes and ketones which permits selective ...