3,2'-吡咯烷基螺吲哚亚胺手性有机催化剂的螺骨架及其在 3-(3-羟基-1-吡唑基)-氧吲哚和多聚甲醛的对映选择性Aldol 缩合反应中的催化评价。
Spiro Scaffold Chiral Organocatalyst of 3,2'-Pyrrolidinyl Spiro-oxindole Amine and Its Catalytic Evaluation in the Enantioselective Aldol Condensation between 3-(3-Hydroxy-1-pyrazol-1-yl)-Oxindole and Paraformaldehyde.
机构信息
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
J Org Chem. 2021 Dec 3;86(23):17371-17379. doi: 10.1021/acs.joc.1c01678. Epub 2021 Nov 16.
The spiro scaffold chiral organocatalyst of 3,2'-pyrrolidinyl spiro-oxindole amine was successfully prepared from racemic spiro-oxindole amine using l-menthol as a chiral pool in 4 steps in 28%-40% overall yields with at least 99% ee in scale-up preparation, and its catalytic activity was evaluated in the enantioselective aldol condensation between 3-(3-hydroxy-1-pyrazol-1-yl)-oxindole and paraformaldehyde. The spiro organocatalyst showed superior catalytic activity and selectivity compared with its counterparts, and most substrates offered good to excellent results with up to 96% yield in 96% ee.
从外消旋的螺环氧化吲哚胺出发，利用 L-薄荷醇作为手性源，成功地制备了螺[吲哚啉-3,2'-吡咯烷]手性有机催化剂，经过 4 步反应，以 28%-40%的总收率得到目标产物，在放大制备中ee 值至少为 99%。在 3-(3-羟基-1-吡唑基)-氧化吲哚和多聚甲醛的对映选择性羟醛缩合反应中评价了其催化活性。与同类催化剂相比，螺有机催化剂表现出更高的催化活性和选择性，大多数底物提供了良好至优秀的结果，ee 值高达 96%，收率高达 96%。
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