74684-65-4Relevant academic research and scientific papers
Expedient and rapid synthesis of 1,2,3-triazolo[5,1-c]morpholines through palladium-copper catalysis
Chowdhury, Chinmay,Mukherjee, Sanjukta,Das, Bimolendu,Achari, Basudeb
supporting information; scheme or table, p. 3612 - 3615 (2009/09/05)
A one-pot approach using palladium - copper as catalyst has been developed for the synthesis of morpholines fused with 1,2,3-triazole. Good regioselectivity, mild reaction conditions, high yields and short reaction time are the hallmarks of this method.
On the use of C2-symmetric aziridines as chiral auxiliaries
Tanner,Birgersson,Gogoll,Luthman
, p. 9797 - 9824 (2007/10/02)
A systematic study has been made of the utility of readily available C2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the axuiliaries can be cleaved off non-destructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.
HIGHLY REGIO AND CHEMOSELECTIVE RING OPENING OF EPOXIDES WITH TRIMETHYLSILYL AZIDE IN THE PRESENCE OF ALUMINIUM ISOPROPOXIDE AND TITANIUM ISOPROPOXIDE
Sutowardoyo, Kun I.,Emziane, Mohamed,Lhoste, Paul,Sinou, Denis
, p. 1435 - 1446 (2007/10/02)
The ring-opening of functionalized epoxides with trimethylsilyl azide in the presence of a catalytic amount of Ti(O-i-Pr)4 or Al(O-i-Pr)3 is described.The reaction is stereospecific and highly regiospecific, leading generally to the formation of the carbon-azido bond on the less substituted carbon.The mechanism of this reaction is also discussed.
