- Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones
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We describe the first atropselective Suzuki-Miyaura cross-coupling of β-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita-Baylis-Hillman reaction is utilized for the Z-selective synthesis of β-keto enol triflates.
- Kumar, Prashant,Shirke, Rajendra P.,Yadav, Sonu,Ramasastry
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p. 4909 - 4914
(2021/06/30)
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- Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester
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The cross-coupling reaction of 3-iodo-4-methoxybenzoic acid methylester with sterically hindered arylboronic esters and especially 5,5-dimethyl-2-mesityl-1,3,2-dioxaborinane, is reported. The optimisation of the process in order to obtain biaryls in good yield by using anhydrous benzene at reflux and sodium phenoxide in the presence of 0.06 equiv. of Pd(PPh3)4 is described. (C) 2000 Elsevier Science Ltd.
- Chaumeil,Signorella,Le Drian
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p. 9655 - 9662
(2007/10/03)
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