N-(Diazoacetyl)oxazolidin-2-thiones as Sulfur-Donor Reagents: Asymmetric Synthesis of Thiiranes from Aldehydes†
Dr. Israel Cano
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Enrique Gómez-Bengoa
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Aitor Landa
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Miguel Maestro
Departamento de Química Fundamental, Facultad de Ciencias, Universidade da Coruña, Campus Zapateira s/n, 15071A Coruña (Spain)
X-Ray analyses.
Search for more papers by this authorDr. Antonia Mielgo
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorIurre Olaizola
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorProf. Dr. Mikel Oiarbide
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorCorresponding Author
Prof. Dr. Claudio Palomo
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)Search for more papers by this authorDr. Israel Cano
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Enrique Gómez-Bengoa
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Aitor Landa
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorDr. Miguel Maestro
Departamento de Química Fundamental, Facultad de Ciencias, Universidade da Coruña, Campus Zapateira s/n, 15071A Coruña (Spain)
X-Ray analyses.
Search for more papers by this authorDr. Antonia Mielgo
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorIurre Olaizola
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorProf. Dr. Mikel Oiarbide
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Search for more papers by this authorCorresponding Author
Prof. Dr. Claudio Palomo
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)Search for more papers by this authorFinancial support was provided by the University of the Basque Country UPV/EHU (UFI 11/22), Basque Government (GV grant No IT-291-07), and Ministerio de Ciencia e Innovación (MICINN, Grant CTQ2007-68095-C02), Spain. A.L. thanks MICINN and the European Social Foundation for a Ramón y Cajal contract. I.O. thanks MCINN for a fellowship. We also thank SGIker (UPV/EHU) for providing NMR, HRMS, X-ray, and computational resources.
Graphical Abstract
Sulfur tyranny: Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N-acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by RhII. Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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