Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 18, Pages 5866-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8011808
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Highly diastereo- and enantioselective additions of substituted alpha-nitroesters to imines have been developed. High diastereoselection relies on the finding that the combination of chiral proton catalyst 2b and alpha-nitro aryl esters bearing 2,6-disubstitution combine to raise substrate-controlled diastereoselection to >20:1 in favor of the syn diastereomer. Furthermore, the chiral catalyst provides enantioselection to the 99% level through control of the addition step in which the azomethine pi-faces are differentiated. The bifunctional chiral protic acid catalyst enables these reactions to proceed without separate preactivation of either substrate, leading to a straightforward synthetic protocol for the formation of alpha,beta-diamino phenyl alanine derivatives.
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