EINE UBERRASCHENDE CIS-SELEKTIVE 1,4-ADDITION VON CYANOCUPRATEN NIEDRIGER ORDNUNG AN OPTISCH AKTIVES 5-(TERT-BUTYLDIMETHYLSILYLOXY)-2-CYCLOHEXENON
作者： Georges Hareau-Vittini , Shinichi Hikichi , Fumie Sato
DOI: 10.1002/(SICI)1521-3757(19980803)110:15<2221::AID-ANGE2221>3.0.CO;2-U
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摘要: Einebemerkenswertecis-Selektivitat wird bei der 1,4-Addition von primaren und sekundaren Alkylcyanocupraten niedriger Ordnung an 5-Siloxy- Benzyloxy-substituierte Cyclohexenone festgestellt. Dies ermoglicht die Synthese beider Enantiomere 5-Alkyl-substituierten Cyclohexenonen, (S)- (R)-3, indem das einfach zugangliche 5-(tert-Butyldimethylsiloxy)-2-cyclohexenon 1 im ersten Schritt entweder mit einem Cyanocuprat oder hoherer umgesetzt wird. DBU=1,8-Diazabicyclo[5.4.0]undec-7-en.
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