Highly stereoselective, one-pot synthesis of azetidines and 2, 4-dioxo-1, 3-diazabicyclo [3.2. 0] compounds mediated by I2

…, CP Dong, M Zhang, WL Ren, Q Meng…

Index: Miao, Chun-Bao; Dong, Chun-Ping; Zhang, Min; Ren, Wen-Long; Meng, Qi; Sun, Xiao-Qiang; Yang, Hai-Tao Journal of Organic Chemistry, 2013 , vol. 78, # 9 p. 4329 - 4340

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Citation Number: 5

Abstract

We report here a convenient method to construct polysubstituted azetidines and 2, 4-dioxo- 1, 3-diazabicyclo [3.2. 0] compounds with high stereoselectivities in a one-pot reaction mediated by I2. The tetramethylguanidine (TMG)/I2-mediated formal [2+ 2] cycloaddition reaction of α-amidomalonate 1 with enones 2 affords functionalized azetidine derivatives 4 in moderate to good yields with high diastereoselectivity. When the α-ureidomalonate 5 is ...