N-Heterocyclic carbene catalyzed asymmetric [3 + 3] cycloaddtion of β,β-disubstituted, α,β-unsaturated carboxylic esters with 3-aminobenzofurans

An N-heterocyclic carbene (NHC) catalyzed formal [3 + 3] cycloaddition reaction of β,β-disubstituted, α,β-unsaturated carboxylic esters with 3-aminobenzofurans is doucumented, furnishing benzofuran fused δ-lactams bearing an all-carbon quaternary stereocenter with moderate to excellent yields and ex...

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Veröffentlicht in:Organic Chemistry Frontiers 2021-04, Vol.8 (7), p.1569-1574
Hauptverfasser: He, Chonglong, Zhou, Yipeng, Li, Zhanhuan, Xu, Jianfeng, Chen, Xingkuan
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Sprache:eng
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Zusammenfassung:An N-heterocyclic carbene (NHC) catalyzed formal [3 + 3] cycloaddition reaction of β,β-disubstituted, α,β-unsaturated carboxylic esters with 3-aminobenzofurans is doucumented, furnishing benzofuran fused δ-lactams bearing an all-carbon quaternary stereocenter with moderate to excellent yields and excellent enantioselectivies. Further gram-scale preparation and synthetic transformation of the cycloadducts demonstrate good practicality and applicability of this β-carbon functionalization reaction.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D0QO01489C