N-(Diazoacetyl)oxazolidin-2-thiones as Sulfur-Donor Reagents: Asymmetric Synthesis of Thiiranes from Aldehydes
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2012
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Wiley
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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.