(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2018

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

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Marie Cordier
Alexis Archambeau

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.
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hal-02093688 , version 1 (09-04-2019)

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Marie Cordier, Alexis Archambeau. (3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes. Organic Letters, 2018, 20 (8), pp.2265-2268. ⟨10.1021/acs.orglett.8b00617⟩. ⟨hal-02093688⟩
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