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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Non-Covalent Carbonyl-Directed Heck-Matsuda Desymmetrizations: Synthesis of Cyclopentene-Fused Spirooxindoles, Spirolactones, and Spirolactams

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Author(s):
Kattela, Shivashankar ; Heerdt, Gabriel ; Correia, Carlos R. D.
Total Authors: 3
Document type: Journal article
Source: ADVANCED SYNTHESIS & CATALYSIS; v. 359, n. 2, p. 260-267, JAN 2017.
Web of Science Citations: 23
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. (AU)

FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 14/05407-4 - Strategies for the dessymmetrization of cyclopentene scaffolds using the enantioselective Heck-Matsuda reaction and their potential synthetic applications.
Grantee:Shivashankar Kattela
Support Opportunities: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC