Highly Enantioselective Alkylation of Allyl Acetates Using Tartrate-Derived Bioxazoline Ligands

Tartrate‐derived bioxazoline ligands, which form a five‐membered chelate ring with metals, were evaluated for use in the asymmetric allylic alkylation (AAA) reactions of various symmetrical and unsymmetrical allyl acetates. Excellent enantioselectivities were achieved by using both symmetrical and u...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-01, Vol.2014 (3), p.606-615
Main Authors: Jayakumar, Samydurai, Prakash, Muthuraj, Balaraman, Kaluvu, Kesavan, Venkitasamy
Format: Article
Language:English
Subjects:
Alkylation
Allylic compounds
Asymmetric synthesis
Enantio­selectivity
Ligands
Palladium
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Summary:Tartrate‐derived bioxazoline ligands, which form a five‐membered chelate ring with metals, were evaluated for use in the asymmetric allylic alkylation (AAA) reactions of various symmetrical and unsymmetrical allyl acetates. Excellent enantioselectivities were achieved by using both symmetrical and unsymmetrical allyl acetates. Palladium(II)‐catalyzed asymmetric allylic alkylation reactions of various symmetrical and unsymmetrical allyl acetates were achieved by using bioxazoline ligands, which were derived from tartaric acid, to give products with excellent enantioselectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301208