220555-55-5Relevant academic research and scientific papers
Stereoselective epoxidation of cyclic alkenes using m-CPBA and Oxone/trifluoroacetone - A comparison
De Sousa,O'Brien,Pilgram,Roder,Towers
, p. 391 - 392 (1999)
A comparison of the observed diastereoselectivity of epoxidation of cyclic alkenes using m-CPBA and Oxone/trifluoroacetone is reported. The results indicate that dioxirane epoxidations are sterically controlled and provide a crude model for determination
Tandem aziridine ring opening-disulfide formation-reduction-Michael addition in one-pot mediated by tetrathiomolybdate
Sureshkumar, Devarajulu,Gunasundari, Thanikachalam,Chandrasekaran, Srinivasan
, p. 7267 - 7281 (2015/08/24)
Abstract A detailed study of tetrathiomolybdate mediated tandem regio- and stereoselective ring opening of aziridine, disulfide formation, reduction of disulfide bond and Michael reaction in a one-pot operation is reported. This constitutes four reactions
Regio- and stereospecific synthesis of β-sulfonamidodisulfides and β-sulfonamidosulfides from aziridines using tetrathiomolybdate as a sulfur transfer reagent
Sureshkumar, Devarajulu,Gunasundari, Thanikachalam,Ganesh, Venkataraman,Chandrasekaran, Srinivasan
, p. 2106 - 2117 (2007/10/03)
A comprehensive study of a general and effective one-step procedure for the synthesis of β-sulfonamidodisulfides directly from N-tosyl aziridines in a regio- and stereospecific manner under neutral conditions without the use of any Lewis acid or base has been reported. This methodology is extended to the synthesis of an optically pure cyclic seven-membered disulfide 29. Synthesis of a variety of β-sulfonamidosulfides involving tandem, multistep reactions in one pot is also reported.
Regio- and stereoselective synthesis of aziridino epoxides from cyclic dienes
Sureshkumar, Devarajulu,Maity, Susama,Chandrasekaran, Srinivasan
, p. 1653 - 1657 (2007/10/03)
Two different routes for the regio- and stereoslective synthesis of aziridino epoxides from cyclic dienes have been explored. The first strategy involves regiospecific aziridination of cyclic diene derivatives and subsequent epoxidation with m-CPBA to yie
Chiral lithium amide base-mediated rearrangement of meso-cyclohexene oxides: Asymmetric synthesis of amino- and aziridinocyclohexenols
O'Brien, Peter,Pilgram, Christopher D.
, p. 523 - 534 (2007/10/03)
Two different chiral lithium amide base routes for the synthesis of amino- and aziridino-containing cyclohexenols have been explored. The first strategy involved the diastereoselective preparation of novel meso-aziridinocyclohexene oxides and their subsequent enantioselective rearrangement using chiral bases. In this approach, the diphenyl-phosphinoyl nitrogen protecting group proved optimal and aziridinocyclohexenols of 47-68% ee were obtained. Of particular note was the smooth rearrangement of the epoxide to an allylic alcohol in the presence of an aziridine: under optimised chiral base conditions, the aziridine remained essentially unaffected. A second more straightforward strategy for introduction of an amino functionality was also investigated: (1S,4R,5S)- and (1R,4R,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2- enols, readily prepared in >95% ee using a chiral base approach, were subjected to Mitsunobu substitution using a sulfonamide and Overman rearrangement.
