A facile and highly diastereoselective aziridination of chiral camphor N-enoylpyrazolidinones with N-aminophthalimide

K. S. Yang; K. Chen

doi:10.1021/jo005621p

A facile and highly diastereoselective aziridination of chiral camphor N-enoylpyrazolidinones with N-aminophthalimide

K. S. Yang, K. Chen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

Reaction of various chiral camphor N-enoylpyrazolidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH₂Cl₂ proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxiliary can be easily recovered in high yields under mild reaction conditions.

Original language	English
Pages (from-to)	1676-1679
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	66
Issue number	5
DOIs	https://doi.org/10.1021/jo005621p
Publication status	Published - 2001 Mar 9

ASJC Scopus subject areas

Organic Chemistry

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title = "A facile and highly diastereoselective aziridination of chiral camphor N-enoylpyrazolidinones with N-aminophthalimide",

abstract = "Reaction of various chiral camphor N-enoylpyrazolidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxiliary can be easily recovered in high yields under mild reaction conditions.",

author = "Yang, {K. S.} and K. Chen",

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AU - Chen, K.

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Y1 - 2001/3/9

N2 - Reaction of various chiral camphor N-enoylpyrazolidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxiliary can be easily recovered in high yields under mild reaction conditions.

AB - Reaction of various chiral camphor N-enoylpyrazolidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH2Cl2 proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxiliary can be easily recovered in high yields under mild reaction conditions.

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A facile and highly diastereoselective aziridination of chiral camphor N-enoylpyrazolidinones with N-aminophthalimide

Abstract

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