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Synthesis of 3-hydroxy and 3-amino 2-substitutedN-heterocyclesvia enamine oxidation and aziridination

✍ Scribed by Mihiro Sunose; Kirsty M. Anderson; A. Guy Orpen; Timothy Gallagher; Simon J.F. Macdonald

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 257 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01915-7

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✦ Synopsis

Reaction of the N-sulfonyl heterocyc/ic enamines (la/b) under asymmetric epoxidation and dihydroxylation reaction conditions leads to 2,3-dihydroxypyrrolidines and piperidines, (2a) and (2b). Only diols are observed undcr aminohydroxylation conditions, but Mn-mediated aziridination of (la) provides a route to the 3-amino-2-methoxypyrrolidine derivatives ( 6)and ( 7).

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