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三重级联策略在手性螺环[3.3]壬醇骨架的立体选择性合成中的应用。

A triple cascade approach towards the diastereoselective synthesis of spiro -decalinol scaffolds.

机构信息

Deparment of Chemistry, School of Applied Sciences and Humanities, Vignan's Foundation for Science Technology and Research-VFSTR (Deemed to be University), Vadlamudi-522 213, Guntur, Andhra Pradesh, India.

出版信息

Chem Commun (Camb). 2022 Sep 15;58(74):10400-10403. doi: 10.1039/d2cc03562f.

Abstract

A [2+2+2] annulation reaction between cyclohexanone, β-nitrostyrene and 2-arylidene-1,3-indanedione afforded multisubstituted spiro -decalinol derivatives in high chemical yields (up to 75%) and excellent diastereoselectivity (up to >20 : 1) at room temperature. This one-pot three-component system follows a triple cascade sequence the Michael/nitro-Michael/Aldol process, resulting in the formation of three C-C bonds, five contiguous stereocenters as well as a spiro quaternary carbon center.

摘要

环己酮、β-硝基苯乙烯和 2-亚苄基-1,3-茚二酮之间的[2+2+2]环加成反应在室温下以高化学收率(高达 75%)和优异的非对映选择性(高达>20:1)得到多取代螺-降莰醇衍生物。该一锅法三组分体系遵循三重级联序列 - Michael/硝基-Michael/Aldol 过程,形成三个 C-C 键、五个连续的立体中心以及螺季碳中心。

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