Remarkably low catalyst loading in Bronsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

被引:273
作者
Rueping, Magnus [1 ]
Antonchick, Andrey P. [1 ]
Theissmann, Thomas [1 ]
机构
[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany
关键词
binol phosphate; Bronsted acids; enantioselective hydrogenation; Hantzsch dihydropyridine; ion-pair catalysis;
D O I
10.1002/anie.200601832
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6751 / 6755
页数:5
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