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Hydrogen Bond Mediated Enantioselectivity of Radical Reactions
Author(s) -
Aechtner Tobias,
Dressel Martina,
Bach Thorsten
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461222
Subject(s) - chemistry , reagent , radical cyclization , hydrogen bond , radical initiator , hydrogen , combinatorial chemistry , reductive elimination , medicinal chemistry , catalysis , photochemistry , organic chemistry , molecule , polymerization , polymer
The chiral complexing reagent 1 used in the reductive cyclization of 3‐(ω‐iodoalkylidene)piperidin‐2‐ones in the presence of Bu 3 SnH and with BEt 3 as the initiator (see scheme) leads to good enantioselectivities thanks to its hydrogen bond mediated association with the radical intermediate. As this example shows, high stereoselectivities are possible for radical reactions proceeding through H‐bonded intermediates.