[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates

Sarah E. Winterton; Joseph M. Ready

doi:10.1021/acs.orglett.6b01104

[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates

Sarah E. Winterton, Joseph M. Ready

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

38 Scopus citations

Abstract

A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diastereoselectivity and stereospecificity allow access to optically active products.

Original language	English (US)
Pages (from-to)	2608-2611
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.6b01104
State	Published - Jun 3 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b01104

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abstract = "A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diastereoselectivity and stereospecificity allow access to optically active products.",

author = "Winterton, {Sarah E.} and Ready, {Joseph M.}",

note = "Funding Information: We would like to thank Dr. M. Kevin Brown (Indiana University) for the suggestion of utilizing ethynyltrimethylsilane. Financial support provided by the NIH (GM102403) and the Welch Foundation (I-1612). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Ready, Joseph M.

N1 - Funding Information: We would like to thank Dr. M. Kevin Brown (Indiana University) for the suggestion of utilizing ethynyltrimethylsilane. Financial support provided by the NIH (GM102403) and the Welch Foundation (I-1612). Publisher Copyright: © 2016 American Chemical Society.

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Y1 - 2016/6/3

N2 - A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diastereoselectivity and stereospecificity allow access to optically active products.

AB - A novel [3 + 2]-cycloaddition between azomethine imines and lithium ynolates is described to synthesize bicyclic pyrazolidinones. These bicyclic pyrazolidinones are versatile intermediates to form β-amino acids and monocyclic pyrazolidinones. High diastereoselectivity and stereospecificity allow access to optically active products.

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[3 + 2]-Cycloadditions of Azomethine Imines and Ynolates

Abstract

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