Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration†
Dr. Nicholas T. Barczak
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorDouglas A. Rooke
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorZachary A. Menard
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorCorresponding Author
Prof. Eric M. Ferreira
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)Search for more papers by this authorDr. Nicholas T. Barczak
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorDouglas A. Rooke
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorZachary A. Menard
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Search for more papers by this authorCorresponding Author
Prof. Eric M. Ferreira
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)
Department of Chemistry, Colorado State University, 1872 Campus Delivery, Fort Collins, CO 80523 (USA)Search for more papers by this authorColorado State University is acknowledged for the support of our program. Eli Lilly is gratefully acknowledged for a graduate research fellowship to D.A.R.
Graphical Abstract
Silicium auf Wanderschaft: Bei der stereoselektiven Bildung von hoch substituierten α-Silyl-β-halogenenonen induziert die elektrophile Aktivierung des Ausgangsalkins durch N-Halogensuccinimide eine anti-selektive Verschiebung der Silylgruppe (siehe Schema). Die resultierenden Enone können leicht und unter Erhaltung der Konfiguration in Alkene mit vier Kohlenstoffsubstituenten umgewandelt werden.
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