期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 26, 期 6, 页码 1794-1802出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.1c00454
关键词
JAK inhibitor; Upadacitinib; enantiosclectivity; 1,3-dipolar cycloaddition; chiral auxiliary
An efficient and elegant enantioselective synthesis of the key chiral pyrrolidine fragment for Upadacitinib (ABT-494) was described using Oppolzer's chiral sultam-directed asymmetric 1,3 dipolar cycloaddition. The method provided the desired level of diastereoselectivity and enantioselectivity in the construction of the 3,4-syn substituted pyrrolidine moiety.
An efficient and elegant enantioselective synthesis of the key chiral pyrrolidine fragment of Upadacitinib (ABT-494) has been described. Oppolzer's chiral sultam-directed asymmetric 1,3 dipolar cycloaddition was employed as a convenient tool to obtain the desired level of concomitant diastereoselectivity and enantioselectivity in the construction of the 3,4-syn substituted pyrrolidine moiety. The synthesis process was demonstrated as a proof of study on a lab scale and was relined during scale-up to allow for easy disengagement of the chiral auxiliary and its subsequent reuse.
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