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Synfacts 2015; 11(4): 0415
DOI: 10.1055/s-0034-1380309
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Addition of Carboxylic Acids Using Chiral Lithium Amides as Auxiliaries

Contributor(s):
Paul Knochel
,
Diana Haas
Lu P, Jackson JJ, Eickhoff JA, Zakarian A * University of California, Santa Barbara, USA
Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries.

J. Am. Chem. Soc. 2015;
137: 656-659
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Further Information

Publication History

Publication Date:
18 March 2015 (online)

 
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Key words

lithium - amides - Michael addition

Significance

Zakarian and co-workers report the direct enantioselective Michael addition of carboxylic acids to α,β-usaturated esters using chiral lithium amides as traceless auxiliaries.


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Comment

The chiral reagents can be readily recovered in 99% yield by extraction with aqueous acid. Additionally, this protocol has been applied to the enantioselective total synthesis of the presumed structure of pulveraven B.


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