180399-94-4Relevant articles and documents
Nucleophilic phosphine-catalyzed [3+2] cycloaddition of allenes with N-(thio)phosphoryl imines and acidic methanolysis of adducts N-(thio)phosphoryl 3-pyrrolines: a facile synthesis of free amine 3-pyrrolines
Zhang, Bo,He, Zhengrong,Xu, Silong,Wu, Guiping,He, Zhengjie
, p. 9471 - 9479 (2008/12/22)
In this report, the dipolarophile imines with easily removable activating group O,O-diethyl(thio)phosphoryl have been investigated in the nucleophilic phosphine-catalyzed [3+2] cycloaddition reaction of electron-deficient allenes. Under the catalysis of a tertiary phosphine, N-(thio)phosphorylimines readily undergo the [3+2] cycloaddition reaction with ethyl 2,3-butadienoate or ethyl 2,3-pentadienoate, affording the corresponding N-(thio)phosphoryl 3-pyrrolines in moderate to high yields with good diastereoselectivity. Removal of the (thio)phosphoryl group from the adducts has been successfully achieved via the acidic methanolysis of the P-N bond, giving the free amine 3-pyrrolines in fair to good yields without severe aromatization. Thus, a facile synthesis of N-unsubstituted 3-pyrrolines is established from the phosphine-catalyzed [3+2] cycloaddition reaction of allenes with imines.
The thermally induced synthesis of N-(diethoxyphosphoryl)aldimines
Zwierzak, Andrzej,Napieraj, Anna
, p. 8789 - 8794 (2007/10/03)
The reaction of diethyl phosphoroamidate (2) with aromatic aldehyde diethyl acetals (1) carried out at 120-160°C provides a simple, one-step preparation of N-(diethoxyphosphoryl)aldimines (3a-b). The extension of this reaction to aliphatic aldehyde diethyl acetals failed to give the expected imines.
