Highly Stereoselective, One-Pot Synthesis of Azetidines and 2,4-Dioxo-1,3-diazabicyclo[3.2.0] Compounds Mediated by I2
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- 作者：Chun-Bao Miao ; Chun-Ping Dong ; Min Zhang ; Wen-Long Ren ; Qi Meng ; Xiao-Qiang Sun ; Hai-Tao Yang
- 刊名：The Journal of Organic Chemistry
- 出版年：2013
- 出版时间：May 3, 2013
- 年：2013
- 卷：78
- 期：9
- 页码：4329-4340
- 全文大小：572K
- 年卷期：v.78,no.9(May 3, 2013)
- ISSN：1520-6904
文摘
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 伪-amidomalonate 1 with enones 2 affords functionalized azetidine derivatives 4 in moderate to good yields with high diastereoselectivity. When the 伪-ureidomalonate 5 is used instead of 1, 2,4-dioxo-1,3-diazabicyclo[3.2.0]heptanes 8 and 2,4-dioxo-1,3-diazabicyclo[3.2.0]heptenes 9 can be prepared selectively through the control of solvent and temperature. 2,4-Dioxo-1,3-diazabicyclo[3.2.0]heptanes 8 can further undergo ring-opening reactions with different nucleophilic reagents to afford the corresponding polyfunctionalized azetidine derivatives 13鈥?b>16 with high steroselectivities.