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Periselectivity Switch of Acylketenes in Cycloadditions with 1-Azadienes: Microwave-Assisted Diastereoselective Domino Three-Component Synthesis of alpha-Spiro-delta-lactams

Marc Presset 1 Yoann Coquerel 1 Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : The microwave-assisted Wolff rearrangement of cyclic 2-diazo-1,3-diketones in the presence of primary amines and alpha,beta-unsaturated aldehydes provides a straightforward three-component stereoselective access to a variety of alpha-spiro-delta-lactams following an imination/Wolff rearrangement/[2 + 4] cycloaddition domino sequence. With aniline derivatives, a complementary aza-Wittig/Wolff rearrangement/[2 + 4] sequence was developed. These reactions feature an unprecedented reactivity of acylketenes as dienophiles in 6 pi electrocyclic processes.
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https://hal.archives-ouvertes.fr/hal-00677643
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Submitted on : Friday, March 9, 2012 - 9:36:36 AM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM

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Marc Presset, Yoann Coquerel, Jean Rodriguez. Periselectivity Switch of Acylketenes in Cycloadditions with 1-Azadienes: Microwave-Assisted Diastereoselective Domino Three-Component Synthesis of alpha-Spiro-delta-lactams. Organic Letters, American Chemical Society, 2010, 12, pp.4212-4215. ⟨10.1021/ol101938r⟩. ⟨hal-00677643⟩

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