Cascade synthesis of (E)-2-alkylidenecyclobutanols

…, A Bandyopadhyay, N Puli, A Kundu, LM Reddy…

Index: Falck; He, Anyu; Manmohan Reddy; Kundu, Abhijit; Barma, Deb K.; Bandyopadhyay; Kamila, Sukanta; Akella, Radha; Bejot, Romain; Mioskowski, Charles Organic Letters, 2006 , vol. 8, # 20 p. 4645 - 4647

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Citation Number: 6

Abstract

To better understand the implications of this unusual cascade reaction, we investigated its scope and possible mechanism and report our findings herein. The reaction parameters were systematically optimized using 1,1,1-trichloroalkane 5, α,β-unsaturated ketone 6, CrCl 2 (6 equiv), and CuCN (1.2 equiv) as the benchmark system. Yields of 7 were best in THF (Table 1, entry 1), somewhat lower in DME, CH 3 CN, and dioxane, and poor in DMF, HMPA, DMSO, and EtOAc. The ...