Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/328047
Type: Artigo
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: Desymmetrization
Enantioselectivity
Heck Reaction
Spiro Compounds
Spirooxindoles
Editor: Wiley-V C H Verlag Gmbh
Weinhem
Citation: Advanced Synthesis & Catalysis. Wiley-v C H Verlag Gmbh, v. 359, p. 260 - 267, 2017.
Rights: fechado
Identifier DOI: 10.1002/adsc.201600946
Address: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600946/full
Date Issue: 2017
Appears in Collections:Unicamp - Artigos e Outros Documentos

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