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Ligand Control in Enantioselective Desymmetrization of Bicyclic Hydrazines: Rhodium(I)‐Catalyzed Ring‐Opening versus Hydroarylation
Author(s) -
Panteleev Jane,
Menard Frederic,
Lautens Mark
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800587
Subject(s) - chemistry , desymmetrization , enantioselective synthesis , rhodium , bicyclic molecule , ring (chemistry) , ligand (biochemistry) , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry
The efficient desymmetrization of 2,3‐bicyclic hydrazines with boronic acids through rhodium‐catalyzed ring‐opening or reductive arylation is described. Excellent levels of enantioselectivity are achieved in ring‐opening with ortho ‐substituted boronic acids, using Josiphos‐type ligands. Alternatively, reductive arylation occurs selectively with electron‐poor Josiphos and Walphos ligands. A CH activation/1,4‐migration mechanism was established through deuterium transfer experiments.