trans‐1‐Sulfonylamino‐2‐isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones
- 17 May 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 12 (16) , 4431-4445
- https://doi.org/10.1002/chem.200501397
Abstract
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.Keywords
This publication has 118 references indexed in Scilit:
- Mechanism of Asymmetric Dialkylzinc Addition to Aldehydes Catalyzed by Titanium(IV) Complexes of N-Sulfonylated β-Amino AlcoholsOrganometallics, 2004
- Recent Advances in the Activation of Boron and Silicon Reagents for Stereocontrolled Allylation ReactionsAngewandte Chemie International Edition in English, 2003
- Catalytic enantioselective allylation of ketones with novel chiral bis‐titanium(IV) catalystChirality, 2002
- Hammett ρ of Reactions of MeLi with BenzophenonesThe Journal of Organic Chemistry, 2002
- From Arene-Catalyzed Lithiation to Other Synthetic AdventuresSynlett, 2001
- New Methodologies Based on Arene-Catalyzed Lithiation Reactions and Their Application to Synthetic Organic ChemistryEuropean Journal of Organic Chemistry, 2000
- Catalytic Asymmetric Addition of ZnPh2 to Ketones: Enantioselective Formation of Quaternary StereocentersJournal of the American Chemical Society, 1998
- Arene-catalysed lithiation reactionsChemical Society Reviews, 1996
- Enantioselective Synthesis of Tertiary Homoallylic Alcohols via Diastereoselective Addition of Allylsilanes to KetonesJournal of the American Chemical Society, 1995
- The Acid-catalyzed Rearrangement of PhenylethynylcarbinolsJournal of the American Chemical Society, 1956