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A Novel Case of Diastereoselection in 5‐ exo Radical Cyclization Promoted by Hydrogen Bonding
Author(s) -
Pedrosa Rafael,
Andrés Celia,
DuqueSoladana Juan P.,
Mendiguchía Pilar
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200011)2000:22<3727::aid-ejoc3727>3.0.co;2-c
Subject(s) - chemistry , tributyltin hydride , enantiopure drug , stereocenter , allylic rearrangement , radical cyclization , alkyl , derivative (finance) , hydride , hydrogen bond , alcohol , stereochemistry , amide , medicinal chemistry , hydrogen , organic chemistry , molecule , enantioselective synthesis , catalysis , financial economics , economics
Moderate stereocontrol in 5‐ exo radical cyclizations of N , N ‐disubstituted (−)‐8‐amino menthol derivatives, promoted by tributyltin hydride and AIBN, was achieved. The stereoselection was explained in terms of hydrogen bond formation in the 1,3‐amino alcohol derivative. The presence of one additional stereocenter at the allylic chain enhanced the stereoselection giving a single cyclization stereoisomer. The cyclization products were easily converted into enantiopure 3‐alkyl‐ or 2,3‐dialkyl‐substituted pyrrolidines.