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Highly stereoselective synthesis of C2-chiral and meso nitroxides from an optically active pyrrolidine by Tomohiro Shibata; Kouhei Uemae; Yukio Yamamoto is a Chemistry article available to read on EtoBox.

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Starting from (2R,5R)-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.

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Author

Tomohiro Shibata; Kouhei Uemae; Yukio Yamamoto

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)