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,The Journal of Organic Chemistry

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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
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-10-20 , DOI: 10.1021/acs.joc.2c00978
Robert W Kubiak ₁ , William F Tracy ₁ , Joshua S Alford ₁ , Huw M L Davies ₁

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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 Rh₂(S-NTTL)₄ or Rh₂(S-DPCP)₄ as the catalysts. These reactions are considered to proceed via rhodium-stabilized donor/acceptor carbene intermediates, and these studies demonstrate that a heteroatom donor group is compatible with an enantioselective transformation.

中文翻译：

4-芳氧基-1-磺酰基-1,2,3-三唑的不对称环丙烷化：将铑稳定的供体/受体卡宾的范围扩展到具有氧供体基团的系统

描述了通过末端烯烃的分子间环丙烷化随后亚胺水解，铑催化对映选择性合成 1-苯氧基环丙烷-1-甲醛。该方法利用 4-芳氧基-1-磺酰基-1,2,3-三唑作为卡宾前体，使用手性四羧酸二铑(II) Rh ₂ ( S -NTTL) ₄或 Rh ₂ ( S -DPCP) ₄作为催化剂。这些反应被认为是通过铑稳定的供体/受体卡宾中间体进行的，并且这些研究表明杂原子供体基团与对映选择性转化相容。

更新日期：2022-10-20

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