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Diastereoselective Chelation‐Controlled Radical Cyclization of Chiral Oxazolidinone‐Derived 2‐Alkenamides and Modeling of the Transition State
Author(s) -
Badone Domenico,
Bernassau JeanMarie,
Cardamone Rosanna,
Guzzi Umberto
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199605351
Subject(s) - van der waals force , chelation , chemistry , radical cyclization , yield (engineering) , radical , force field (fiction) , transition state , computational chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis , computer science , thermodynamics , physics , artificial intelligence
A good yield, but only modest diastereoselectivity ( 2:3 = 45:55) is achieved in the radical cyclization of 1 to give 2 and 3 . MgBr 2 ·Et 2 O was essential for good diastereoselectivity ( 2:3 = 82:18). Transition state modeling with a specifically developed “radical force‐field” suggested that the observed diastereoselectivities can be ascribed to van der Waals attractive interactions between arenes.