Chiral ligand optimization in the asymmetric zirconium-zinc transmetalation aldehyde addition reaction

Wipf, P and Jayasuriya, N (2008) Chiral ligand optimization in the asymmetric zirconium-zinc transmetalation aldehyde addition reaction. Chirality, 20 (3-4). 425 - 430. ISSN 0899-0042

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Abstract

The in situ hydrozirconation-transmetalation-aldehyde addition process is a convenient method for the generation of allylic alcohols. Ongoing research has focused on enhancing the enantioselectivity and substrate scope of this process. A chiral β-amino thiol scaffold was evaluated in the addition reaction. Amino thiols tend to provide the highest ee's, in part due to the higher affinity of sulfur for zinc over zirconium. A class of valine-based thiol ligands was identified to be effective for the formation of enantiomerically enriched allylic alcohols in terms of low ligand loading and high % ee. © 2007 Wiley-Liss, Inc.

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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Wipf, P pwipf@pitt.edu PWIPF Jayasuriya, N
Date:	3 March 2008
Date Type:	Publication
Journal or Publication Title:	Chirality
Volume:	20
Number:	3-4
Page Range:	425 - 430
DOI or Unique Handle:	10.1002/chir.20468
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
ISSN:	0899-0042
PubMed ID:	17823948
Date Deposited:	01 Jul 2014 17:19
Last Modified:	02 Feb 2019 15:57
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/20680

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