Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes
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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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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
Almendros, P
[1
]
Aragoncillo, C
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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
Aragoncillo, C
[1
]
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[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
DABCO promoted reactions of various activated vinyl systems with optically pure 4-oxoazetidine-2-carbaldehydes 1 gave rise to Baylis-Hillman adducts 3 With excellent syn stereoselectivities, without detectable racemization. Products 3 are used. for the asymmetric preparation of unusual 2-azetidinones fused to medium-sized rings via chemo- and Stereocontrolled divergent radical cyclization. The formation of bicyclic beta -lactams 4-6 could be rationalized through a tandem radical Michael addition/endo cyclization or a tandem radical addition/Michael addition, depending pn the electronic nature of the radical promoter.