Accessing Skeletal Diversity under Iron Catalysis using Substrate Control: Formation of Pyrroles versus Lactones

被引:32
作者
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
Teresa Quiros, M. [1 ]
机构
[1] Univ Complutense Madrid, Fac Quim, Grp Lactamas & Heterociclos Bioact,CSIC, Unidad Asociada,Dept Quim Organ 1, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, Consejo Super Invest Cient, E-28006 Madrid, Spain
关键词
alkynes; allenes; iron; pyrroles; rearrangement; METHYLENE-GAMMA-BUTYROLACTONES; BETA-LACTAMS; BUILDING-BLOCKS; C-C; STEREOSELECTIVE-SYNTHESIS; ALPHA-ALLENOLS; HYDROAMINATION; CYCLIZATION; CHEMISTRY; SYNTHON;
D O I
10.1002/adsc.201100049
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
2-Azetidinone-tethered alkynols and allenols, readily prepared from a propanylidene beta-lactam aldehyde, were used as starting materials for divergent ring expansion reactions catalyzed by iron(III) chloride. Worthy of note, in contrast to the iron-catalyzed reactions of beta-lactam allenols which lead to gamma-lactones, the reaction of beta-lactam alkynols under identical conditions gives pyrroles. The gold-catalyzed 6-endo aminocyclization of these allenic gamma-lactones formed fused dihydropyridines. The iron-catalyzed formation of pyrroles may proceed through a Meyer-Schuster rearrangement followed by beta-lactam ring opening and cyclization by attack of the amino group to the ketone.
引用
收藏
页码:585 / 594
页数:10
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