Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 17, Pages 3311-3325Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200456
Keywords
asymmetric Michael addition; chiral organocatalysts; key intermediates; trandolapril; ss,gamma-unsaturated alpha-keto esters
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Funding
- National Nature Science Foundation of China [20972095, 21172143, 21172145]
- Science and Technology Commission of Shanghai Municipality [10dz1910105]
- Nippon Chemical Industrial Co., Ltd.
- Instrumental Analysis Center of Shanghai Jiao Tong University
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(2S,3aR,7aS)-Perhydroindolic acid, the key intermediate in the synthesis of trandolapril, and its trans-isomers, were readily prepared. These proline-like molecules are unique in that they contain a rigid bicyclic structure, with two hydrogen atoms trans to each other at the bridgehead carbon atoms. These molecules were used successfully as chiral organocatalysts in asymmetric domino Michael addition/cyclization reactions of aldehyde esters with beta,gamma-unsaturated a-keto esters. They proved to have excellent catalytic behavior, allowing for the synthesis of multi-substituted, enantiomerically enriched hemiacetal esters. Under optimal conditions (using 10 mol% catalyst loading), a series of beta,gamma-unsaturated a-keto esters was examined with up to 99% de, ee and yield, respectively. Additionally, the enantiomerically enriched hemiacetal esters could be readily transformed into their corresponding bioactive pyrano[2,3-b]pyrans (possessing a multi-substituted bicyclic backbone).
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