Chemodivergence in Enantioselective Desymmetrization of Diazabicycles: Ring‐Opening versus Reductive Arylation | Zendy

Menard Frederic | Zendy; Lautens Mark | Zendy

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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).

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