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Type: Outro documento
Title: Non-covalent carbonyl-directed heck-matsuda desymmetrizations: synthesis of cyclopentene-fused spirooxindoles, spirolactones, and spirolactams
Author: Kattela, Shivashankar
Heerdt, Gabriel
Correia, 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
Subject: Enantiosseletividade
Reação de Heck
Country: Alemanha
Editor: John Wiley & Sons
Rights: Fechado
Identifier DOI: 10.1002/adsc.201600946
Date Issue: 2017
Appears in Collections:IQ - Artigos e Outros Documentos

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