通过配体控制的立体发散的分子内 Tsuji-Trost 烯丙基化反应来立体选择性合成β-内酰胺。
Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation.
机构信息
Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands.
Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
出版信息
J Org Chem. 2020 Aug 7;85(15):9566-9584. doi: 10.1021/acs.joc.0c00575. Epub 2020 Jul 13.
The diastereoselective synthesis of highly substituted β-lactams by intramolecular Tsuji-Trost allylation is reported. Judicious selection of the ligand on palladium allows selective access to either the isomer (in generally good to excellent yield with very high diastereomeric excess) or isomer (with yields and diastereoselectivity ranging from modest to excellent depending on the substrate). The reaction proceeds under exceedingly mild conditions (rt, no additives) with a broad range of substrates, which are readily accessible by the Ugi reaction.
报道了通过分子内 Tsuji-Trost 烯丙基化反应进行高取代的β-内酰胺的非对映选择性合成。对钯上配体的明智选择允许选择性地得到 either 异构体（通常具有非常高的非对映选择性，收率很好到优秀）或 异构体（根据底物的不同，产率和非对映选择性范围从中等到优秀）。该反应在非常温和的条件下（rt，无添加剂）进行，具有广泛的底物范围，这些底物可以通过 Ugi 反应很容易地获得。
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