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

Cano Rico, Israel; Gómez-Bengoa, Enrique; Landa, Aitor; Maestro, Miguel; Mielgo, Antonia; Olaizola, Iurre; Oiarbide, Mikel; Palomo, Claudio

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

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Asymmetric_Synthesis_of_Thiiranes_from_Aldehydes.pdf (4.12 MB)

Official URL

https://doi.org/10.1002/anie.201204771

Publication date

2012

Authors

Cano Rico, Israel

Gómez-Bengoa, Enrique

Publisher

Wiley

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URI

https://hdl.handle.net/20.500.14352/93578

Citation

I. Cano, E. Gómez-Bengoa, A. Landa, M. Maestro, A. Mielgo, I. Olaizola, M. Oiarbide, C. Palomo. N-(Diazoacetyl)oxazolidin-2-thiones as sulfur donor reagents: Asymmetric synthesis of thiiranes from aldehydes. Angew. Chem., Int. Ed. 2012, 51, 10856-10860

Abstract

We reported the first Rh-catalyzed reaction of a diazoacetyl compound with aldehydes that affords thiiranes, instead of oxiranes, as known before. This unusual reactivity relied on the use of N-(diazoacetyl)oxazolidin-2-thiones as new chiral sulfur-donor reagents and enabled the direct production of optically active thiiranes with very high stereoselectivity.