Copper-Catalyzed Asymmetric Hydrogenation of Aryl and Heteroaryl Ketones

Copper-Catalyzed Asymmetric Hydrogenation of Aryl and Heteroaryl Ketones
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DOI:
10.1021/ol4021223
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发表时间:
2013-09-06
期刊:
影响因子:
5.2
通讯作者:
Johnson, Jeffrey S.
Johnson, Jeffrey S.
中科院分区:
化学1区
文献类型:
--
作者:
Krabbe, Scott W.;Hatcher, Mark A.;Johnson, Jeffrey S.

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高通量筛选使得能够开发用于前手性芳基和杂芳基酮的不对称氢化的Cu基催化剂体系,其在低至5巴的H-2压力下操作。(R,S)-N-Me-3,5-二甲苯基-BoPhoz和三(3,5-二甲苯基)膦配体的组合以良好的产率和对映选择性提供苄醇。辅助的三芳基膦的电子和空间特性在决定反应性和选择性方面是重要的。
High throughput screening enabled the development of a Cu-based catalyst system for the asymmetric hydrogenation of prochiral aryl and heteroaryl ketones that operates at H-2 pressures as low as 5 bar. A ligand combination of (R,S)-N-Me-3,5-xylyl-BoPhoz and tris(3,5-xylyl)phosphine provided benzylic alcohols in good yields and enantioselectivities. The electronic and steric characteristics of the ancillary triarylphosphine were important in determining both reactivity and selectivity.