All about topology control: The title reaction yields valuable tetrahydrofuran spirooxindoles (see scheme; TMS=trimethylsilyl), and exemplifies a rare asymmetric 1,6-addition to linear 2,4-dienals proceeding with high δ-site- and stereoselectivity. A steering group at the β-dienal position ensured molecular preorganization of the catalytically active vinylogous iminium ion intermediate for highly predictable reaction outcomes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Silvi M., Chatterjee I., Liu Y., Melchiorre P. (2013). Controlling the molecular topology of vinylogous iminium ions by logical substrate design: Highly regio- and stereoselective aminocatalytic 1,6-addition to linear 2,4-dienals. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 52(41), 10780-10783 [10.1002/anie.201305870].
Controlling the molecular topology of vinylogous iminium ions by logical substrate design: Highly regio- and stereoselective aminocatalytic 1,6-addition to linear 2,4-dienals
Melchiorre P.
Ultimo
Supervision
2013
Abstract
All about topology control: The title reaction yields valuable tetrahydrofuran spirooxindoles (see scheme; TMS=trimethylsilyl), and exemplifies a rare asymmetric 1,6-addition to linear 2,4-dienals proceeding with high δ-site- and stereoselectivity. A steering group at the β-dienal position ensured molecular preorganization of the catalytically active vinylogous iminium ion intermediate for highly predictable reaction outcomes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
