(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Marie Cordier; Alexis Archambeau

doi:10.1021/acs.orglett.8b00617

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Marie Cordier
, Alexis Archambeau

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

Abstract

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

Original language	English
Pages (from-to)	2265-2268
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.8b00617
Publication status	Published - 20 Apr 2018
Externally published	Yes

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10.1021/acs.orglett.8b00617

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title = "(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes",

abstract = "Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.",

author = "Marie Cordier and Alexis Archambeau",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b00617",

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AU - Archambeau, Alexis

PY - 2018/4/20

Y1 - 2018/4/20

N2 - Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

AB - Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

U2 - 10.1021/acs.orglett.8b00617

DO - 10.1021/acs.orglett.8b00617

M3 - Article

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AN - SCOPUS:85045896433

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Abstract

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