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

Marie Cordier 1 Alexis Archambeau 2
1 LCM - Laboratoire de chimie moléculaire
2 DCSO - Laboratoire de synthèse organique
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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Submitted on : Tuesday, April 9, 2019 - 10:35:48 AM
Last modification on : Thursday, June 20, 2019 - 10:14:02 AM

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

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