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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.)

Regio- and diastereoselective Pd-catalyzed aminochlorocyclization of allylic carbamates: scope, derivatization, and mechanism

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Author(s):
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Papa Spadafora, Bruna [1] ; Moreira Ribeiro, Francisco Wanderson [2, 3] ; Matsushima, Jullyane Emi [1] ; Ariga, Elaine Miho [1] ; Omari, Isaac [2] ; Soares, Priscila Machado Arruda [1] ; de Oliveira-Silva, Diogo [1] ; Vinhato, Elisangela [1] ; McIndoe, J. Scott [2] ; Carita Correra, Thiago ; Rodrigues, Alessandro [1]
Total Authors: 11
Affiliation:
[1] Univ Fed Sao Paulo, Dept Chem, UNIFESP Prof Artur Riedel St 275, Lab 10, BR-09972270 Diadema, SP - Brazil
[2] Univ Victoria, Dept Chem, POB 3065, Victoria, BC V8W 3V6 - Canada
[3] Univ Sao Paulo, Inst Chem, Dept Fundamental Chem, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 19, n. 25 JUN 2021.
Web of Science Citations: 0
Abstract

The regio- and diastereoselective synthesis of oxazolidinones via a Pd-catalyzed vicinal C-N/C-Cl bond-forming reaction from internal alkenes of allylic carbamates is reported. The oxazolidinones are obtained in yields of 44 to 95% with high to excellent diastereoselectivities (from 6 : 1 to >20 : 1 dr) from readily available precursors. This process is scalable, and the products are suitable for the synthesis of useful amino alcohols. A detailed theoretical and experimental mechanistic study was carried out to describe that the reaction proceeds through an anti-aminopalladation of the alkene followed by an oxidative C-Pd(ii) cleavage with retention of the carbon stereochemistry to yield the major diastereomer. The role of Cu(ii) in a C-Cl bond-forming mechanism step has also been proposed. (AU)

FAPESP's process: 19/16026-5 - Cyclization reactions promoted by Pd/Cu Catalysts
Grantee:Francisco Wanderson Moreira Ribeiro
Support Opportunities: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 16/21676-0 - Enantioselective haloamination reactions aiming the synthesis of aminodiols
Grantee:Alessandro Rodrigues
Support Opportunities: Regular Research Grants
FAPESP's process: 15/08539-1 - Multi-User Equipment approved in grant 2014/15962-5: ion trap mass spectrometer modified to perform infrared vibrational spectroscopy (IRMPD)
Grantee:Thiago Carita Correra
Support Opportunities: Multi-user Equipment Program
FAPESP's process: 16/17328-7 - Enantioselective haloamination reactions aiming aminodiols synthesis
Grantee:Bruna Papa Spadafora
Support Opportunities: Scholarships in Brazil - Master
FAPESP's process: 17/18485-1 - Mechanistic studies of haloamination reactions promoted by metallic and organic catalysts
Grantee:Francisco Wanderson Moreira Ribeiro
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy
Grantee:Thiago Carita Correra
Support Opportunities: Research Grants - Young Investigators Grants
FAPESP's process: 19/25634-9 - Real-time reaction analysis in complex matrices by advanced mass spectrometry techniques
Grantee:Thiago Carita Correra
Support Opportunities: Regular Research Grants