C 2 ‐Symmetrical Pyrrolidine Derivatives Chiral Auxiliaries in Radical Chemistry
1993; Wiley; Volume: 76; Issue: 1 Linguagem: Inglês
10.1002/hlca.19930760128
ISSN1522-2675
AutoresA. VEIT, Roman Lenz, M. Seiler, Markus Neuburger, Margareta Zehnder, Bernd Giese,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAbstract Fumaramides 3b and 3c bearing the C 2 ‐symmetrical pyrrolidine moieties (2 R ,5 R )‐2,5‐bis(methoxymethyl)pyrrolidine ( 2b ) or 1,3:4,6‐di‐ O ‐benzylidene‐2,5‐dideoxy‐2,5‐imino‐ L ‐idit ( 2c ), respectively, as a chiral auxiliary lead to high diastereoselectivities in radical reactions (‘tin method’; Scheme 1 ). Removal of the chiral auxiliaries affords the corresponding alkylated fumaric acids Scheme 2 . Single‐crystal X‐ray structures of 3b and 3c support arguments that lead to the model of 1,4‐stereoinduction.
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