One-pot synthesis of enantiomerically enriched 2,3-disubstituted cyclopentanones via copper-catalyzed 1,4-reduction and alkylation.
[reaction: see text]. Enantiomerically enriched 2,3-disubstituted cyclopentanones were prepared via copper-catalyzed 1,4-reduction of 3-substituted cyclopentenones followed by alkylation of the resulting silyl enol ether. Using this procedure, trans-2,3-disubstituted cyclopentanones were produced in moderate to good overall yields (42-67%) and with excellent enantiomeric and diastereomeric excesses. The reduction and alkylation were performed in a single reaction vessel.
Yun
J
J
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
S L
SL
D000477:Alkylating Agents / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D008956:Models, Chemical
D000477:Alkylating Agents; D003517:Cyclopentanes; C007201:cyclopentanone; D003300:Copper