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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:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
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.pitt.edu/id/eprint/20680

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