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Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined
Author(s) -
Wang Jiang,
Shao PanLin,
Lin Xin,
Ma Baode,
Wen Jialin,
Zhang Xumu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006661
Subject(s) - enantiopure drug , kinetic resolution , stereocenter , chemistry , substrate (aquarium) , asymmetric hydrogenation , combinatorial chemistry , enantioselective synthesis , catalysis , organic chemistry , oceanography , geology
An unprecedented Ir/f‐amphox‐catalyzed asymmetric hydrogenation of racemic 2,3‐ syn ‐dihydroxy‐1,4‐diones is presented involving dynamic kinetic resolution, which produces (1 R ,2 R ,3 R ,4 R )‐tetraols. This protocol constitutes an efficient and straightforward approach to accessing sugar alcohols bearing four contiguous stereocenters. The strategy exhibits various advantages over existing methods, including excellent yields (up to 98 %), exceptional stereoselectivities (up to 99:1 dr, 99.9 % ee ), operational simplicity and substrate generality. Moreover, the nature of the reaction was revealed as a stepwise transformation by in situ Fourier‐transform infrared spectroscopy and isolation of intermediates.