relation: http://d-scholarship-dev.library.pitt.edu/20444/
title: On the role of chiral catalysts in the alkenyl zirconocene/zinc addition to aldehydes: A study of ligand loading and asymmetric amplification
creator: Wipf, P
creator: Jayasuriya, N
creator: Ribe, S
description: Unusual nonlinear asymmetric amplification and chiral ligand loading effects were discovered for the use of catalytic quantities of chiral aminoalcohols in the in situ hydrozirconation - transmetalation - aldehyde addition processes. While the stereochemically most efficient aminothiol ligands demonstrated mechanistically conventional reaction parameters in excellent agreement with Kagan's ML2 system, the asymmetric induction in the presence of a chiral aminoalcohol was found to vary greatly with loading and %ee of the ligand. Aminothiols remain the ligands of choice for the highly enantioselective formation of allylic alcohols and provide experimentally more predictable reaction variables. However, new, optimized conditions lead to a synthetically useful product %ee using the readily available and scalable aminoalcohol 2a. © 2003 Wiley-Liss, Inc.
date: 2003-01-01
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/20444/1/licence.txt
identifier:   Wipf, P and Jayasuriya, N and Ribe, S  (2003) On the role of chiral catalysts in the alkenyl zirconocene/zinc addition to aldehydes: A study of ligand loading and asymmetric amplification.  Chirality, 15 (3).  208 - 212.  ISSN 0899-0042     
relation: 10.1002/chir.10176