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|Title:||Non-covalent Carbonyl-directed Heck-matsuda Desymmetrizations: Synthesis Of Cyclopentene-fused Spirooxindoles, Spirolactones, And Spirolactams|
Carlos R. D.
|Abstract:||Enantioselective carbonyl-directable Heck reactions using aryldiazonium salts were developed with the aim to construct chiral quaternary spiro centers in an efficient manner. Five-and six-membered spirooxindoles, spirolactones, and spirolactams (36 examples) were obtained in good to excellent isolated yields with diastereoselectivities ranging from 13:1 to >20:1, and enantiomeric excesses up to 99% in short reaction times (1.0-1.5 h) under mild conditions (40 degrees C). A rationale for the diastereo- and enantioselectivity based on an unprecedented non-covalent carbonyl group directing effect is also presented, and supported by computational calculations.|
|Editor:||Wiley-V C H Verlag Gmbh|
|Citation:||Advanced Synthesis & Catalysis. Wiley-v C H Verlag Gmbh, v. 359, p. 260 - 267, 2017.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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