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
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.
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.
