Optically Active 2,3-Allenoates via Palladium-Catalyzed Carbonylation of Enantioenriched Propargylic Mesylates

Optically Active 2,3-Allenoates via Palladium-Catalyzed Carbonylation of Enantioenriched Propargylic Mesylates
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通过对映体富集的丙炔甲磺酸酯的钯催化羰基化得到光学活性 2,3-联烯酸酯

DOI:
10.1002/adsc.201200910
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发表时间:
2013
影响因子:
5.4
通讯作者:
Shengming Ma
Shengming Ma
中科院分区:
化学2区
文献类型:
--
作者:
Yuli Wang;Shengming Ma

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在温和的条件下,以(S)‐(−)‐5,5′‐双(二苯基膦)- 4,4′‐双- 1,3‐苯二氮唑[(S)‐SEGPHOS] (3 mol%)为催化剂,以磷酸氢二铵(1.1等量)为碱,以(S)‐二苯基膦](3 mol%)为催化剂,以(S)‐二苯基膦](3 mol%)为底物,由对映体富集的丙炔甲磺酸为原料合成了具有光学活性的2,3‐丙烯酸酯,收率中至优异,手性转移效率高。
Under mild conditions, optically active 2,3‐allenoates were synthesized from enantioenriched propargylic mesylates with moderate to excellent yields and high efficiency of chirality transfer by using palladium(0) bis(dibenzylideneacetone) (3 mol%) with (S)‐(−)‐5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole [(S)‐SEGPHOS] (3 mol%) as the catalyst and diammonium hydrogen phosphate (1.1 equiv .) as the base.