Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles
Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles
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DOI：
10.1002/chem.201601198
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发表时间：
2016-05-04
影响因子：
4.3
通讯作者：
Breit, Bernhard
中科院分区：
文献类型：
--
作者：
Haydl, Alexander M.;Hilpert, Lukas J.;Breit, Bernhard
吡唑衍生物与内部和末端炔烃的铑催化不对称N选择性偶联具有最大的化学、区域和对映选择性，可得到对映体纯烯丙基吡唑，可轻松掺入小分子药物中。该方法的特点是底物范围广泛，从而与各种不同的官能团具有显着的兼容性。此外，它还展示了仅一步即可实现区域选择性、位置选择性和对映选择性的有趣案例，强调了通过从各种内部和末端炔烃产生的烯丙基化吡唑的高度灵活的方法，仅合成了多达六种可能产物中的一种。
The rhodium-catalyzed asymmetric N-selective coupling of pyrazole derivatives with internal and terminal alkynes features an utmost chemo-, regio-, and enantioselective access to enantiopure allylic pyrazoles, readily available for incorporation in small-molecule pharmaceuticals. This methodology is distinguished by a broad substrate scope, resulting in a remarkable compatability with a variety of different functional groups. It furthermore exhibits an intriguing case of regio-, position-, and enantioselectivity in just one step, underscoring the sole synthesis of just one out of up to six possible products in a highly flexible approach to allylated pyrazoles by emanating from various internal and terminal alkynes.