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Article Abstract
We report a Cu(II)-(,)-Pr-FOXAP-catalyzed borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone for the synthesis of highly substituted and functionalized all-carbon spiroindane boronates under mild conditions. A series of optically active spiroindanes bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities (≤97% ee) and diastereoselectivities (up to >20:1 dr). In addition, scale-up synthesis of this method and synthetic transformations of spiroindane boronates are also illustrated.
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| http://dx.doi.org/10.1021/acs.orglett.2c02955 | DOI Listing |
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Enantio- and Diastereoselective Cu(II)-Catalyzed Conjugate Borylation/Michael Addition Cascade: Synthesis of Spiroindane Boronates.
Org Lett
October 2022
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.
We report a Cu(II)-(,)-Pr-FOXAP-catalyzed borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone for the synthesis of highly substituted and functionalized all-carbon spiroindane boronates under mild conditions. A series of optically active spiroindanes bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities (≤97% ee) and diastereoselectivities (up to >20:1 dr). In addition, scale-up synthesis of this method and synthetic transformations of spiroindane boronates are also illustrated.
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