[2,2]Paracyclophane-BasedN,O-Ligands in Alkenylzinc Additions to Aldehydes
- 20 November 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (25) , 4119-4122
- https://doi.org/10.1021/ol016954r
Abstract
The application of planar and central chiral [2,2]paracyclophane-based N,O-ligands in asymmetric alkenylzinc additions to various aldehydes is described, which gives rise to very high ee's especially for difficult substrates. A fine-tuning of the alkenylzinc species by employing different transmetalation reagents is reported, allowing control of the steric bulk of the alkenylzinc species and thus the selectivity of the catalysis.Keywords
This publication has 14 references indexed in Scilit:
- Asymmetric, Catalytic Phenyl Transfer to Aldehydes: Enantioselective Synthesis of DiarylmethanolsPublished by Wiley ,2000
- Zirconocene−Zinc Transmetalation and in Situ Catalytic Asymmetric Addition to AldehydesThe Journal of Organic Chemistry, 1998
- Addition of Organozincate Reagents to Imines Derived from (S)‐1‐Phenylethylamine and Ethyl (S)‐Valinate—Synthesis of (S)‐1‐(2‐Pyridyl)AlkylaminesChemistry – A European Journal, 1997
- Preparation of allylic alcohols by alkene transfer from zirconium to zincTetrahedron Letters, 1994
- Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcoholsTetrahedron Letters, 1991
- Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and AmplificationAngewandte Chemie International Edition in English, 1991
- Enantioselective synthesis of sec-allylalcohols by catalytic asymmetric addition of divinylzinc to aldehydes.Tetrahedron Letters, 1988
- Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydesJournal of the American Chemical Society, 1986
- Gemischte organozinkverbindungen durch austauschreaktionen von diorganozinkverbindungenJournal of Organometallic Chemistry, 1985
- 13C-NMR Spectroscopy of Mixed Dialkylzinc Compounds with Prochiral Alkyl ResiduesAngewandte Chemie International Edition in English, 1985