(1S,7S)-2-(Phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene

[195604-55-8] C13H14O3S (MW 250.31) InChI = 1S/C13H14O3S/c14-17(15,10-6-2-1-3-7-10)12-9-5-4-8-11-13(12)16-11/h1-3,6-7,9,11,13H,4-5,8H2 InChIKey = XCSYOXSQTQNAQZ-UHFFFAOYSA-N (−)(enantiomer) [474094-59-2] InChI = 1S/C13H14O3S/c14-17(15,10-6-2-1-3-7-10)12-9-5-4-8-11-13(12)16-11/h1-3,6-7,9,11,13H,4-5,8H2 InChIKey = XCSYOXSQTQNAQZ-UHFFFAOYSA-N ( + )-(S,S)(enantiomer) [0] InChI = 1/C13H14O3S/c14-17(15,10-6-2-1-3-7-10)12-9-5-4-8-11-13(12)16-11/h1-3,6-7,9,11,13H,4-5,8H2/t11-,13-/m0/s1 InChIKey = XCSYOXSQTQNAQZ-AAEUAGOBBM ( + )-(R,R)(enantiomer) [150130-51-1] InChI = 1S/C13H14O3S/c14-17(15,10-6-2-1-3-7-10)12-9-5-4-8-11-13(12)16-11/h1-3,6-7,9,11,13H,4-5,8H2/t11-,13-/m1/s1 InChIKey = XCSYOXSQTQNAQZ-DGCLKSJQSA-N (racemic) (used as a scaffold for asymmetric synthesis of complex molecules) Alternate Name: 8-oxabicyclo[5.1.0]oct-2-ene, (2-phenyl sulfonyl)-, (1S,7S)-. Physical Data: mp 84.0–85.0 °C. Solubility: soluble in most common organic solvents (THF, Et2O, benzene, CH2Cl2, etc.); insoluble in water. Form Supplied in: white or off-white crystalline solid; commercially available through Aldrich Chemical Co.; typical impurity in <3% is diene precursor. Analysis of Reagent Purity: characterized by 1H, 13C NMR; ee and purity determined by Chiral HPLC using ChiralPaq AD 4.6 × 50 mm2 column eluting with 10% 2-propanol/hexane, flow rate 1.0 mL/min, (S,S) product retention time 8.1 min, and (R,R) enantiomer retention time 5.3 min. [α]25D = + 68, c = 18.5 mg/mL. Preparative Methods: prepared in 80–90% yield from 2-Benzenesulfonylcyclohepta-1,3-diene via a modified asymmetric Jacobsen epoxidation using the (R,R)-Mn-Salen complex [(R,R)-( + )-N,N′- bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride].1 Purification: readily recrystallized from MeOH; can also be purified via silica gel column chromatography. Handling, Storage, and Precautions: air and water stable and can be stored indefinitely under nitrogen at 0 °C. No special handling is required. May be harmful in case of inhalation, ingestion, or skin absorption, and can cause eye and skin irritation. Should be used in a well-ventilated hood and contact with eyes or skin should be avoided.