A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone

Benjamin E. Stephens; Fei Liu

doi:10.1021/jo8018285

A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone

Benjamin E. Stephens, Fei Liu^*

^*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

(Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.

Original language	English
Pages (from-to)	254-263
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	74
Issue number	1
DOIs	https://doi.org/10.1021/jo8018285
Publication status	Published - 2 Jan 2009

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title = "A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone",

abstract = "(Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66\% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.",

author = "Stephens, \{Benjamin E.\} and Fei Liu",

year = "2009",

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doi = "10.1021/jo8018285",

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AU - Stephens, Benjamin E.

AU - Liu, Fei

PY - 2009/1/2

Y1 - 2009/1/2

N2 - (Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.

AB - (Chemical Equation Presented) A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available γ-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.

UR - https://www.scopus.com/pages/publications/58149289852

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M3 - Article

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VL - 74

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IS - 1

ER -

A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from γ-butyrolactone

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