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
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Abstract
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.
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