Gill Mamta, Das Arko, Singh Vinod K
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India.
Org Lett. 2022 Aug 12;24(31):5629-5634. doi: 10.1021/acs.orglett.2c01438. Epub 2022 Jul 29.
An enantioselective (3+2) cycloaddition reaction of iminoesters occurring with opposite regioselectivity is reported. This reaction provides chiral polysubstituted pyrrolidines with high enantioselectivities (up to 97%), diastereoselectivities (>20:1), and yields (up to 99%). Interestingly, changing the alpha-substituents of the iminoesters from an aryl to an aliphatic (benzyl) group or hydrogen resulted in the formation of normal (3+2) cycloaddition products, also in excellent enantioselectivities.
报道了亚胺酯的对映选择性(3 + 2)环加成反应，该反应具有相反的区域选择性。此反应能提供具有高对映选择性(高达97%)、非对映选择性(>20:1)和产率(高达99%)的手性多取代吡咯烷。有趣的是，将亚胺酯的α-取代基从芳基变为脂肪族(苄基)基团或氢，也能以优异的对映选择性生成正常的(3 + 2)环加成产物。
