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首頁> 外文OA文獻 >Quinine-catalyzed asymmetric domino Michael-cyclization reaction for the synthesis of spirocyclic oxindoles bearing two spiro quaternary centers and three consecutive stereocenters.
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Quinine-catalyzed asymmetric domino Michael-cyclization reaction for the synthesis of spirocyclic oxindoles bearing two spiro quaternary centers and three consecutive stereocenters.

機譯:奎寧催化的不對稱多米諾骨牌邁克爾環(huán)化反應,用于合成帶有兩個螺四價中心和三個連續(xù)立體中心的螺環(huán)羥吲哚。

摘要

An efficient organocatalytic diastereo- and enantioselective method for the construction of spirocyclic oxindole derivatives bearing two Spiro quaternary centers and three consecutive stereocenters via a domino Michael/cyclization process has been developed. Using commercially available quinine as catalyst, the reactions of 3-isothiocyanato oxindoles with unsaturated pyrazolones and unsaturated isoxazolones proceeded smoothly under mild reaction conditions for giving two classes of spirocyclic oxindole compounds in high to excellent yields with moderate to good diastereoselectivities and enantioselectivities. A plausible dual activation working model was tentatively proposed to account for the stereochemistry of the domino Michael/cyclization process. (C) 2014 Published by Elsevier Ltd.
機譯:已經開發(fā)出一種有效的有機催化非對映和對映選擇性的方法,用于通過多米諾米歇爾/環(huán)化過程構建帶有兩個Spiro季中心和三個連續(xù)的立體中心的螺環(huán)羥吲哚衍生物。使用市售的奎寧作為催化劑,3-異硫氰酸根合吲哚類化合物與不飽和吡唑啉酮和不飽和異惡唑酮的反應在溫和的反應條件下順利進行,從而以中等至良好的非對映選擇性和對映選擇性高收率地獲得了兩類螺環(huán)惡吲哚化合物。暫時提出了一個可行的雙重激活工作模型來解釋多米諾米歇爾/環(huán)化過程的立體化學。 (C)2014由Elsevier Ltd.出版

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