Highly Stereoselective, One-Pot Synthesis of Azeticlines and 2,4-Dioxo-1,3-diazabicyclo[3.2.0] Compounds Mediated by l<subscript>2</subscript>.
In: Journal of Organic Chemistry, Jg. 78 (2013-05-03), Heft 9, S. 4329-4340
Online
academicJournal
Zugriff:
We report here a convenient method to construct polysubstituted azetidines and 2,4-dioxo-1,3-diazabi-cydo[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 mnctionalized azetidine derivatives 4 in moderate to good yields with high diastereoselectivity. When the a-ureidomalonate 5 is used instead of 1, 2,4-dioxo-l,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-l,3-diazabicyclo[3.2.0]heptanes 8 can further undergo ring-opening reactions with different nucleophilic reagents to afford the corresponding polyfunctionalized azetidine derivatives 13-16 with high steroselectivities. [ABSTRACT FROM AUTHOR]
Titel: |
Highly Stereoselective, One-Pot Synthesis of Azeticlines and 2,4-Dioxo-1,3-diazabicyclo[3.2.0] Compounds Mediated by l<subscript>2</subscript>.
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Autor/in / Beteiligte Person: | Miao, Chun-Bao ; Dong, Chun-Ping ; Zhang, Min ; Ren, Wen-Long ; Meng, Qi ; Sun, Xiao-Qiang ; Yang, Hai-Tao |
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Zeitschrift: | Journal of Organic Chemistry, Jg. 78 (2013-05-03), Heft 9, S. 4329-4340 |
Veröffentlichung: | 2013 |
Medientyp: | academicJournal |
ISSN: | 0022-3263 (print) |
DOI: | 10.1021/jo400181r |
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