Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 4, Pages 1562-1566Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912140
Keywords
aldol reaction; alkynylogous reaction; allenes; asymmetric catalysis; copper
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Funding
- Thousand Youth Talents Plan
- National Natural Science Foundation of China [21672235, 21871287, 21922114]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS Key Laboratory of Synthetic Chemistry of Natural Substances
- Shanghai Institute of Organic Chemistry
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Chiral 2,3-allenols were constructed through copper(I)-catalyzed asymmetric direct alkynylogous aldol reaction. With aromatic and heteroaromatic aldehydes, the alkynylogous aldol reaction with (R)-DTBM-SEGPHOS as the ligand proceeded smoothly to furnish the products in excellent regioselectivity with good to high diastereoselectivity and excellent enantioselectivity. In the cases of aliphatic aldehydes, esters of but-2-yn-1-ol as the substrates and (R,R)-Ph-BPE as the ligand were found to be crucial to get good to high regio- and diastereoselectivity. The produced chiral 2,3-allenols are easily transformed into synthetically useful 2-furanones through cyclization. Finally, the developed method was successfully applied in the rapid synthesis of two chiral intermediates toward the synthesis of two pharmaceutically active compounds that have been proposed for the treatment of neurological disorders.
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