期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 10, 页码 3043-3046出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410723
关键词
asymmetric catalysis; cycloaddition; dienamines; organocatalysis; ylides
资金
- Spanish MINECO [CTQ2011-22790]
- Spanish MINECO (Juan de la Cierva contract)
- Basque Government [IT328-10, OSALAN14/02]
- UPV/EHU [UFI QOSYC 11/22, EHUA12/09]
Benzopyrylium ylides generated in situ from 1-acetoxyisochroman-4-ones reacted with ,-unsaturated aldehydes in the presence of a bifunctional secondary-amine/squaramide catalyst to furnish [5+2] cycloaddition products in good yield with high diastereo- and enantioselectivity. The reaction proceeds by dienamine activation and involves ,-functionalization of the enal. The dienamine intermediates showed exclusive ,-reactivity and provided direct access to compounds with the 8-oxabicyclo[3.2.1]octane framework. The ability of the bifunctional secondary-amine/squaramide catalyst to engage in hydrogen-bonding interactions with the ylide made it particularly effective in terms of both the yield and the stereoselectivity of the transformation.
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