T. Shibata, Kouhei Uemae, Yukio Yamamoto*
Jun 16, 2000
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract Starting from (2 R ,5 R )-2,5-bis(methoxymethyl)pyrrolidine 1 , hydroxylamine cis - 3 was synthesized with high stereoselectivity by successive oxidation and addition of PhMgBr. By using PhLi, trans ( C 2 -chiral) pyrrolidine nitroxide trans - 7 was obtained from nitrone 5 derived from hydroxylamine 3 . The cis ( meso ) counterpart cis - 7 was produced along with trans - 7 when PhMgBr was employed in place of PhLi. Moreover, cis - 7 was also obtained selectively by using PhLi and Et 2 AlCl with nitrone 5 . The change of stereochemical bias observed when EtMgBr and/or nitrone 10 bearing an ethyl group were employed is also discussed.