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N-(Diazoacetyl)oxazolidin-2-thiones as Sulfur-Donor Reagents: Asymmetric Synthesis of Thiiranes from Aldehydes

Authors

  • Dr. Israel Cano,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Dr. Enrique Gómez-Bengoa,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Dr. Aitor Landa,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Dr. Miguel Maestro,

    1. Departamento de Química Fundamental, Facultad de Ciencias, Universidade da Coruña, Campus Zapateira s/n, 15071A Coruña (Spain)
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    • X-Ray analyses.

  • Dr. Antonia Mielgo,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Iurre Olaizola,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Prof. Dr. Mikel Oiarbide,

    1. Departamento de Química Orgánica I, Universidad del País Vasco, Manuel Lardizabal 3, 20018 San Sebastián (Spain)
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  • Prof. Dr. Claudio Palomo

    Corresponding author
    1. 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)
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  • Financial 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.

Abstract

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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.

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