4-芳氧基-1-磺酰基-1,2,3-三唑的不对称环丙烷化反应：扩展铑稳定给体/受体卡宾到具有氧给体基团的体系的范围。
Asymmetric Cyclopropanation with 4-Aryloxy-1-sulfonyl-1,2,3-triazoles: Expanding the Range of Rhodium-Stabilized Donor/Acceptor Carbenes to Systems with an Oxygen Donor Group.
机构信息
Department of Chemistry, Emory University, 1515 Dickey Dr., Atlanta, Georgia 30329, United States.
出版信息
J Org Chem. 2022 Nov 4;87(21):13517-13528. doi: 10.1021/acs.joc.2c00978. Epub 2022 Oct 20.
Abstract
Rhodium-catalyzed enantioselective synthesis of 1-phenoxycyclopropane-1-carbaldehydes by intermolecular cyclopropanation of terminal alkenes followed by imine hydrolysis is described. This methodology utilizes 4-aryloxy-1-sulfonyl-1,2,3-triazoles as the carbene precursors and the chiral dirhodium(II) tetracarboxylates Rh(-NTTL) or Rh(-DPCP) as the catalysts. These reactions are considered to proceed rhodium-stabilized donor/acceptor carbene intermediates, and these studies demonstrate that a heteroatom donor group is compatible with an enantioselective transformation.
摘要
铑催化的通过末端烯烃的分子间环丙烷化反应再水解亚胺构建 1-苯氧基环丙烷-1-甲醛的对映选择性合成方法。该方法利用 4-芳氧基-1-磺酰基-1,2,3-三唑作为卡宾前体，手性二铑（II）四羧酸酯 Rh(-NTTL)或 Rh(-DPCP)作为催化剂。这些反应被认为是通过铑稳定的给体/受体卡宾中间体进行的，这些研究表明杂原子给体基团与对映选择性转化相容。
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