Polymer-Supported BINOL Ligand for the Titanium-Catalyzed Diethylzinc Addition to Aldehydes: A Remarkable Positive Influence of the Support on the Enantioselectivity of the Catalyst
- 1 January 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (2) , 295-296
- https://doi.org/10.1021/jo990771p
Abstract
A new polymer-supported BINOL (1,1'-Bi-2-naphthol) was synthesized by coupling of aminomethyl polystyrene resin and (S)-2, 2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid. This new ligand was found to be more enantioselective for the asymmetric addition of diethylzinc to aldehydes than its "free" analog [Ti(BINOL)(i)PrO(2)]. A range of 57-99% ee's as well as 78-97% yields was obtained, and the electronic properties of the enantioselectivity were also observed.Keywords
This publication has 16 references indexed in Scilit:
- Significant Effects of Nonconjugated Remote Substituents in Catalytic Asymmetric EpoxidationJournal of the American Chemical Society, 1998
- Novel Asymmetric Alkylation of Aromatic Aldehydes with Triethylaluminum Catalyzed by Titanium·(1,1‘-bi-2-naphthol) and Titanium·(5,5‘,6,6‘,7,7‘,8,8‘-octahydro-1,1‘- bi-2-naphthol) ComplexesJournal of the American Chemical Society, 1997
- N,N,N′,N′-Tetraalkyl-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxamides: Novel Chiral Auxiliaries for Asymmetric Simmons–Smith Cyclopropanation of Allylic Alcohols and for Asymmetric Diethylzinc Addition to AldehydesBulletin of the Chemical Society of Japan, 1997
- Enantioselective Addition of Diethylzinc to Aldehydes Using 1,1′-Bi-2-naphthol-3,3′-dicarboxamide as a Chiral AuxiliaryChemistry Letters, 1996
- Continuous Asymmetric Synthesis in a Membrane ReactorAngewandte Chemie International Edition in English, 1996
- A General Solid-Phase Synthesis Strategy for the Preparation of 2-Pyrrolidinemethanol LigandsThe Journal of Organic Chemistry, 1995
- Novel electronic effects of remote substituents on the oxazaborolidine-catalyzed enantioselective reduction of ketonesTetrahedron Letters, 1995
- Changes of enantioselectivity with the substrate ratio for the addition of diethylzinc to aldehydes using a catalyst coupled to a soluble polymerJournal of the Chemical Society, Perkin Transactions 1, 1995
- Practical synthesis of BINAP-ruthenium(II) dicarboxylate complexesThe Journal of Organic Chemistry, 1992
- New solid-phase catalysts for asymmetric synthesis: cross-linked polymers containing a chiral Schiff base-zinc complexThe Journal of Organic Chemistry, 1990