Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes.

Synthesis of novel C2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes

Novel chiral bis(oxazoline) ligands bearing dibenzo[a,c]cycloheptadiene and a dihydroxy group have been synthesized and their application in the catalytic asymmetric addition of diethylzinc to aldehydes investigated. The enantioselectivities for the aromatic aldehydes are generally high and up to 96% ee was obtained. 2003 Elsevier Ltd. All rights reserved.

Asymmetric Preparation of D-Phg-L-Pro Dipeptide-derived Chiral Ligands for Enantioselective Addition of Diethylzinc to Aldehydes

Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by a Titanate Complex with a Chiral Tetradentate Ligand.

The addition of dialkylzincs to aldehydes is one of the most widely studied carbon-carbon bond-forming reactions. Many systems reported to date use amino alcohols as ligands and zinc complexes as catalysts.1 The asymmetric version of this alkylation reaction can also be catalyzed by chiral titanate complexes2-4 (e.g., TADDOLs2 and chiral sulfonamides3). We have recently studied a titanate compl...

Design of novel chiral N,N,O-tridentate phenanthroline ligands and their application to enantioselective addition of organozinc reagents to aldehydes.

The novel N,N,O-tridentate phenanthroline ligand (BinThro) bearing an axially chiral binaphthyl backbone prepared from BINOL was found to be an effective chiral catalyst for enantioselective addition of diethylzinc to aromatic aldehydes with high enantioselectivity (up to 95% ee).

Aziridine sulfides and disulfides as catalysts for the enantioselective addition of diethylzinc to aldehydes.

Chiral aziridine sulfides and disulfides were synthesized from readily available and inexpensive R-cysteine by a Mitsunobu reaction; their application in the addition of diethylzinc to aldehydes provides secondary alcohols with up to 99% ee and S-configuration.