DBU-Promoted Dynamic Kinetic Resolution in Rh-Catalyzed Asymmetric Transfer Hydrogenation of 5-Alkyl Cyclic Sulfamidate Imines: Stereoselective Synthesis of Functionalized 1,2-Amino Alcohols

被引：15

作者：

Kim, Hyeong Rae ^{[1
,2
]}

Achary, Raghavendra ^{[1
]}

Lee, Hyeon-Kyu ^{[1
,2
]}

机构：

[1] Korea Res Inst Chem Technol, Korea Chem Bank, POB 107, Yuseong 305600, Daejeon, South Korea

[2] Univ Sci & Technol, Dept Med Chem & Pharmacol, 113 Gwahango, Yuseong 305333, Daejeon, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

OXIDATIVE OLEFINATION-CYCLIZATION; ALPHA-HYDROXYLATION; 1,3-DISUBSTITUTED ISOINDOLINES; ENANTIOSELECTIVE SYNTHESIS; KETONES; SULFAMIDATE-5-CARBOXYLATES; NOREPHEDRINE; MECHANISM;

D O I：

10.1021/acs.joc.8b01892

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dynamic kinetic resolution (DKR)-driven asymmetric transfer hydrogenation of 5-alkyl cyclic sulfamidate imine produces the corresponding sulfamidate with excellent levels of diastereo- and enantioselectivity by employing a HCO2H/DBU mixture as the hydrogen source in the presence of the Noyori-type chiral Rh-catalyst at room temperature for 1 h. In this process, DKR was induced by DBU-promoted rapid racemization of the substrate. Stereoselective transformations of the resulting cyclic sulfamidates to functionalized enantiomerically enriched 1,2-amino alcohol and chiral amine substances are also described.

引用

页码：11987 / 11999

页数：13

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