(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

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.

Domains: Chemical Sciences; Organic chemistry

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⟩