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Dinuclear Zinc Synergistic Catalytic Asymmetric Phospha-Michael/Michael Cascade Reaction: Synthesis Of Chiral 1,2,3- Trisubstituted Indanes Bearing Phosphorus Group

Posted on:2020-10-05Degree:MasterType:Thesis
Country:ChinaCandidate:B K TaoFull Text:PDF
GTID:2381330575955328Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Indane,as a privileged skeleton,has been found in various natural and synthetic products.Indane derivatives,especially chiral indane compounds,have captivated chemists' extensive attention in several science disciplines due to their unique biological and pharmaceutical activities.In this thesis,we have reported a new and efficient catalytic asymmetric Phospha-Michael/Michael cascade reaction of o-dienones and dialkyl phosphates using a dinuclear zinc cooperative catalyst.A series of new chiral 1,2,3-trisubstituted indane derivatives bearing phosphoryl groups are obtained with excellent diastereoselectivities(>99:1 dr)and excellent enantioselectivities(>99% ee)in the presence of 10 mol% dinuclear zinc catalyst under mild conditions.In addition,this process can run on a gram scale without impacting its stereoselectivities.Finally,a possible mechanism for the reaction is proposed.Further,efforts will be focused on determining the absolute configuration of the products and the biological evaluation of these adducts in our group.
Keywords/Search Tags:indane derivatives, dinuclear zinc, Phosphoa-Michael/Michael cascade reaction, 1?2?3-trisubstituted indane derivatives, stereoselectivities, enantioselectivities
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