An Enantioselective Organocatalytic Oxidative Dearomatization Strategy

Abstract

Supporting Information Experimental procedures and data 1 H and 13 C NMR spectra General Experimental 1 H NMR spectra were recorded on a Bruker DPX 400 spectrometer in deuterochloroform (CDCl 3 ), unless stated otherwise, operating at 400 MHz. 13 C NMR spectra were recorded on a Bruker DPX 400 spectrometer operating at 100 MHz. Chemical shifts (δ) are quoted relative to residual solvent (CHCl 3 , δ = 7.26 ppm for 1 H and δ = 77.0 for 13 C of CDCl 3 ) and coupling constants (J) are corrected and quoted to the nearest 0.1 Hz. The following abbreviation are used to indicate the multiplicity of the signals: s = singlet; d = doublet; t = triplet; q = quartet; qn = quintet; m = multiplet; br = broad; app = apparent; and associated combinations, e.g. dd = doublet of doublets. The temperature of the acquisition of the NMR spectra was 298 ± 3K. DEPT135 and 2dimensional experiments (COSY, HMBC and HMQC) were used to support assignments where appropriate but are not included. High resolution mass spectra (HRMS) were measured on a Micromass Q-TOF spectrometer using EI (electron impact) or ES (electrospray ionisation) techniques at the Department of Chemistry, University of Cambridge or at the EPSRC Mass Spectrometry Service at the University of Swansea. Infared (IR) spectra were recorded on a Perkin Elmer 1FT-IR Spectrometer fitted with an ATR sampling accessory as neat films, either through direct application or deposited in CHCl 3 . Optical rotations were measured in CHCl 3 on a Perkin Elmer 343 Polarimeter; [α] D values are reported in 10 -1 degrees cm 2 g -1 at 589 nm. Chiral HPLC analysis was performed on HP Agilent 1100 apparatus. Melting points (m.p.) were recorded using a Reichert hot stage apparatus and are reported uncorrected. All anhydrous solvents were solvents were dried by standard techniques and freshly distilled before use. Diethyl ether and tetrahydrofuran were distilled from lithium aluminium hydride; acetonitrile, dichloromethane and toluene from calcium hydride; and triethylamine from potassium hydroxide. N, N-dimethylformamide and dimethyl sulfoxide were purchased in anhydrous form. All flash chromatography was carried out using dry packed Merck 9385 Kieselgel 60 silica gel. Reactions monitored by thin layer chromatography (t.l.c.) were carried out on Kieselgel 60 PF 254 (Merck) 0.2 mm plates.All reagents were purified by standard procedures or used as obtained from commercial sources.Reactions were carried out using oven dried glassware and under an atmosphere of nitrogen unless otherwise stated.

Ein einfaches Rezept für raffinierte Cocktails: organokatalysierte Eintopf‐Reaktionen – Konzept, Nomenklatur und Ausblick

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Die asymmetrische Aminokatalyse – Goldrausch in der organischen Chemie

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“…The optimum reagent was found to be hypervalent iodine reagent PhI(OAc) 2 (Scheme 30) [101]. The reaction was extended to biarylphenol to obtain comparable results to benzo-fused structures like 100.…”