Tetramethylsilane → 2,3-dihydro-1H-inden-2-yl sulfamate

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반응 단계

NBS was recrystallized from water according to the guidelines of Armarego and Chai (Armarego, W. L. F. and Chai, C. L. L. (2003) In: Purification of Laboratory Chemicals; 5th ed., Elsevier Science: New York. p-TsNH2 and K2CO3 (anhydrous, granular) were used as received. Olefins (except Entries 10 and 11, Table 1) were filtered over a plug of alumina and distilled prior to use. Trans-2-phenyl-1-vinylcyclopropane 9 was prepared according the procedure of Fu, et al. (1991) (“MECHANISTIC STUDY OF A SYNTHETICALLY USEFUL MONOOXYGENASE MODEL USING THE HYPERSENSITIVE PROBE TRANS-2-PHENYL-1-VINYLCYCLOPROPANE,” J. Org. Chem. 56(23):6497-6500). Sulfamate indan-2-yl ester 7 was prepared according to the procedure of Espino, et al. (2001) (“Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C—H Bond Oxidation,” J. Am. Chem. Soc. 123(28):6935-6936) 2-Vinylbenzenesulfonamide (Entry 10, Table 1) and 2-allylbenzenesulfonamide (Entry 11, Table 1) were prepared according the procedure of Dauban and Dodd (Dauban, P. et al. (2000) “SYNTHESIS OF CYCLIC SULFONAMIDES VIA INTRAMOLECULAR COPPER-CATALYZED REACTION OF UNSATURATED IMINOIODINANES,” Org. Lett. 2(15):2327-2329). Dirhodium(II,II) caprolactamate [Rh2(cap)4.2CH3CN] was prepared as previously described (Doyle, M. P. et al. (1993) “ELECTRONIC AND STERIC CONTROL IN CARBON-HYDROGEN INSERTION REACTIONS OF DIAZZOACETOACETATES CATALYZED BY DIRHODIUM(II) CARBPXYLATES AND CARBOXAMIDES,” J. Am. Chem. Soc. 115(3):958-964). 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were obtained on a Bruker DRX-400 NMR as solutions in CDCl3. Chemical shifts are reported in parts per million (ppm, δ) downfield from Me4Si (TMS); coupling constants are reported in Hertz (Hz). UV-Visible spectra were obtained on a Varian Cary 50 spectrophotometer using a xenon flash lamp. Preparative chromatographic purification was performed using SiliCycle (60 Å, 40-63 mesh) silica gel according to the method of Still, W. C. et al. (1978) (“RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION,” J. Org. Chem. 43(14):2923-2925). Thin layer chromatography (TLC) was performed on Merck 0.25 mm silica gel 60 F254 plates with visualization by fluorescence quenching or aqueous KMnO4 stain. Anhydrous CH2Cl2 was purified prior to use by nitrogen forced-flow over activated alumina as described by Pangbom, A. B. et al. (1996) (“SAFE AND CONVENIENT PROCEDURE FOR SOLVENT PURIFICATION,” Organometallics 15(5): 1518-1520).

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