新型氮杂-π-烯丙基钯两性离子中间体的非对映和对映选择性(3 + 2)环加成反应
Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate.
作者信息
Scuiller Anaïs, Casaretto Nicolas, Archambeau Alexis
机构信息
Laboratoire de Synthèse Organique, UMR 7652, CNRS, Ecole Polytechnique, ENSTA Paris, Institut Polytechnique de Paris, 91128 Palaiseau Cedex, France.
Laboratoire de Chimie Moléculaire, UMR 9168, CNRS, Ecole Polytechnique, Institut Polytechnique de Paris, 91128 Palaiseau Cedex, France.
出版信息
J Org Chem. 2023 Jul 21;88(14):9941-9945. doi: 10.1021/acs.joc.3c00707. Epub 2023 Jul 9.
Cycloaddition of azaoxyallyl cations or other C─(C═O)─N synthon precursors is a well-established route toward lactams and other -heterocycles, but despite the wide synthetic scope of this approach, enantioselective versions remain scarce. We herein report 5-vinyloxazolidine-2,4-diones (VOxD) as a suitable precursor of a new palladium-π-allylpalladium intermediate. In the presence of electrophilic alkenes, (3 + 2) γ-lactam cycloadducts could be formed with a high level of diastereo- and enantioselectivity.
氮杂氧代烯丙基阳离子或其他C─(C═O)─N合成子前体的环加成反应是合成内酰胺和其他含氮杂环化合物的成熟方法，但尽管该方法具有广泛的合成范围，对映选择性版本仍然很少。我们在此报道5-乙烯基恶唑烷-2,4-二酮（VOxD）作为一种新型钯-π-烯丙基钯中间体的合适前体。在亲电烯烃存在下，可以以高非对映选择性和对映选择性形成(3 + 2) γ-内酰胺环加成物。
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