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trans ‐1‐Sulfonylamino‐2‐isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones
Author(s) -
Forrat Vicente J.,
Prieto Oscar,
Ramón Diego J.,
Yus Miguel
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501397
Subject(s) - enantioselective synthesis , transmetalation , reagent , chemistry , aryl , enantiomer , catalysis , combinatorial chemistry , alkyl , organic chemistry
The catalytic enantioselective addition of different organozinc reagents (such as alkyl and aryl derivatives or in situ generated aryl, allyl alkenyl, and alkynyl derivatives obtained through different transmetallation processes) to simple ketones has been accomplished by using titanium tetraisopropoxide and chiral ligands derived from substituted trans ‐1‐sulfonylamino‐2‐isoborneolsulfonylaminocyclohexane, producing the corresponding tertiary alcohols with enantiomeric excesses ( ee ) up to >99 %. A simple and efficient procedure for the synthesis of the chiral ligands used in these reactions is described.