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Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-07-12 , DOI: 10.1002/anie.202006661
Jiang Wang 1, 2 , Pan-Lin Shao 2, 3 , Xin Lin 3 , Baode Ma 2, 3 , Jialin Wen 2, 4 , Xumu Zhang 2
Affiliation  

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 (1R,2R,3R,4R)‐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.

中文翻译:

对映纯糖醇的简便合成:不对称氢化和动态动力学拆分相结合。

提出了空前的Ir / f-氨撑氧催化外消旋2,3-顺式-二羟基-1,4-二酮的不对称氢化反应,涉及动态动力学拆分,产生(1 R,2 R,3 R,4 R)-四元醇。该协议构成了访问带有四个连续立体中心的糖醇的有效且直接的方法。该策略与现有方法相比具有多种优势,包括出色的产率(高达98%),出色的立体选择性(高达99:1 dr,99.9%ee)),操作简便和基板通用性。此外,通过原位傅里叶变换红外光谱法和中间体的分离,反应的性质被揭示为逐步转变。
更新日期:2020-07-12
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