Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides
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作者:
Alcaide, B
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Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, SpainUniv Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Alcaide, B
[1
]
Almendros, P
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机构:Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Almendros, P
Alonso, JM
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机构:Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Alonso, JM
Aly, MF
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机构:Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Aly, MF
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[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] S Valley Univ, Fac Sci, Dept Chem, Qena, Egypt
This work describes a convenient procedure for the straightforward preparation of polyfunctionalized enantiopure pyrrolizidine systems. The methodology capitalizes on a HCl(g)-promoted reaction of the 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides, smoothly affording different types of highly functionalized bi- and tricyclic systems in racemic and optically pure forms. This process involves a selective bond cleavage of the four-membered ring, followed by a rearrangement under the reaction conditions. The synthetic route employed was shown to be compatible with a variety of 4-oxoazetidine-2-carbaldehydes, ol-amino esters, or dipolarophiles, offering a versatile entry to pyrrolizidine systems.