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Chemodivergence in Enantioselective Desymmetrization of Diazabicycles: Ring‐Opening versus Reductive Arylation
Author(s) -
Menard Frederic,
Lautens Mark
Publication year - 2008
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.200704708
Subject(s) - desymmetrization , enantioselective synthesis , ring (chemistry) , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
Divergent bicycle paths : A chemodivergent desymmetrization occurs after an initial enantioselective carbometalation step. The reaction brings a solution to the challenging problem of the enantioselective ring‐opening of diazabicyclo[2.2.1]heptanes to obtain arylated cyclopentenamines (see scheme, right). An alternative reaction pathway was discovered in which CH insertion/1,4‐metal migration occurs to give reductive arylation products (left).