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Chiral ligand optimization in the asymmetric zirconium–zinc transmetalation aldehyde addition reaction
Author(s) -
Wipf Peter,
Jayasuriya Nilukshi
Publication year - 2008
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20468
Subject(s) - transmetalation , chemistry , aldehyde , allylic rearrangement , ligand (biochemistry) , chirality (physics) , zirconium , chiral ligand , thiol , combinatorial chemistry , enantioselective synthesis , zinc , reagent , organic chemistry , catalysis , biochemistry , receptor , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The in situ hydrozirconation–transmetalation‐aldehyde addition process is a convenient method for the generation of allylic alcohols. Ongoing research has focused on enhancing the enantioselectivity and substrate scope of this process. A chiral β‐amino thiol scaffold was evaluated in the addition reaction. Amino thiols tend to provide the highest ee 's, in part due to the higher affinity of sulfur for zinc over zirconium. A class of valine‐based thiol ligands was identified to be effective for the formation of enantiomerically enriched allylic alcohols in terms of low ligand loading and high % ee . Chirality, 2008. © 2007 Wiley‐Liss, Inc.