Asymmetric Synthesis of α,β-Epoxy-γ-lactams
through Tandem Darzens/Hemiaminalization Reaction

Feng, Xiaoming

Asymmetric Synthesis of α,β-Epoxy-γ-lactams through Tandem Darzens/Hemiaminalization Reaction

Posted on 2019-06-11 - 17:46

A catalytic asymmetric tandem Darzens/hemiaminalization reaction of glyoxals with α-bromo-β-esteramides or α-bromo-β-ketoamide was accomplished in the presence of a chiral N,N′-dioxide/Yb(III) complex. Various chiral α,β-epoxy-γ-lactams were obtained in moderate to good yields with excellent diastereo- and enantioselectivities. The versatility of the transformation is illustrated in the formal synthesis of berkeleyamide D.

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Shen, Bin; Liu, Wen; Cao, Weidi; Liu, Xiaohua; Feng, Xiaoming (2019). Asymmetric Synthesis of α,β-Epoxy-γ-lactams through Tandem Darzens/Hemiaminalization Reaction. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b01589

https://doi.org/10.1021/acs.orglett.9b01589

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