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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.)

Enantioselective Oxy-Heck-Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (-)-Conocarpan

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Author(s):
Silva, Allan R. [1] ; Polo, Ellen C. [1] ; Martins, Nelson C. [1] ; Correia, Carlos Roque D. [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, UNICAMP, Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ADVANCED SYNTHESIS & CATALYSIS; v. 360, n. 2, p. 346-365, JAN 17 2018.
Web of Science Citations: 16
Abstract

This work discloses the first examples of an effective enantioselective oxy-Heck-Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck-Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (-)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (-)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck-Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck-Matsuda reactions is also presented. (AU)

FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 13/25886-1 - Enantioselective Heck-Matsuda reaction involving styrenics systems: trans-dihydrobenzofurans substituted synthesis
Grantee:Allan Ribeiro da Silva
Support type: Scholarships in Brazil - Doctorate
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 type: Research Projects - Thematic Grants
FAPESP's process: 13/17083-6 - New applications of the Enantioselective Heck Reaction using Arenediazonium Salts
Grantee:Nelson Cabrita Martins
Support type: Scholarships in Brazil - Post-Doctorate