Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions

Jorin Hoogenboom; Han Zuilhof; Tom Wennekes

doi:10.1021/acs.orglett.5b02662

Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions

Jorin Hoogenboom
, Han Zuilhof
, Tom Wennekes^*

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.

Original language	English
Pages (from-to)	5550-5553
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02662
Publication status	Published - 2015

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abstract = "A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.",

author = "Jorin Hoogenboom and Han Zuilhof and Tom Wennekes",

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doi = "10.1021/acs.orglett.5b02662",

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AU - Hoogenboom, Jorin

AU - Zuilhof, Han

AU - Wennekes, Tom

PY - 2015

Y1 - 2015

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AB - A new masked aldehyde-containing nitrone 1 that is easily available through a facile one-step procedure has been developed. It undergoes a [3 + 2]-thermal cycloaddition with a wide range of dipolarophiles, affording isoxazolidine cycloadducts that are suitable for versatile postcycloaddition modifications. The acetal cycloadducts are acid-stable, but allow for acetal hydrolysis under mildly basic conditions. The isoxazolidine ring can be opened via an efficient one-pot procedure to give amine-protected γ-alcohols that can be further converted to furanose derivatives.

U2 - 10.1021/acs.orglett.5b02662

DO - 10.1021/acs.orglett.5b02662

M3 - Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Versatile Scope of a Masked Aldehyde Nitrone in 1,3-Dipolar Cycloadditions

Abstract

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