rings3 - THREE-MEMBERED RING FORMATION 3 Membered Rings 1...

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THREE-MEMBERED RING FORMATION 125 3 Membered Rings 1. epoxides a. peracids, hydroperoxides and dioxiranes b. transition metal catalyzed epoxidations c. halohydrins d. Darzen's condensation e. sulfur ylides 2. cyclopropanes a. Simmons-Smith reactions b. diazo compounds c. sulfur ylides d. S N 2 displacements 3. aziridines a. nitrenes b. S N 2 displacements Epoxides - peracid, hydroperoxide and dioxirane oxidation of alkenes - transition metal catalyzed epoxidation of alkenes - Sharpless epoxidation - Metal oxo reagents (Jacobsen's reagent) - from halohydrins NBS, H 2 O Br OH base O bromohydrin - Darzen's Condensation BrCH 2 CO 2 Et B: BrCHCO 2 Et _ R R' O R R' O - Br CO 2 Et R' CO 2 Et O R - sulfur ylides Chem. Rev. 1997 , 97 , 2421. S O CH 2 - Me Me Me 2 SCH 2 - + + Ph S O CH 2 - NMe 2 SPh 2 _ + Corey Johnson sulfoximine Trost
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THREE-MEMBERED RING FORMATION 126 - dimethylsulfoxonium methylide and dimethylsulfonium methylide (Corey's reagent) review: Tetrahedron 1987 , 43 , 2609. R
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rings3 - THREE-MEMBERED RING FORMATION 3 Membered Rings 1...

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