期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 358, 期 11, 页码 1848-1853出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600039
关键词
cycloaddition; diastereoselectivity; kinetic resolution; Morita-Baylis-Hillman adducts; rhodium
资金
- Spanish Ministry of Education and Science (MINECO) [CTQ2014-54306-P, CTQ2012-32436]
- DIUE of the Generalitat de Catalunya [2014SGR931]
- Generalitat de Catalunya
A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent chiral centres (quaternary and tertiary, respectively) were obtained with complete diastereoselectivity and high enantioselectivity (84-97%) through a kinetic resolution of the M-B-H adduct. Furthermore, these highly substituted cyclohexadienes reacted with dienophiles to afford the corresponding Diels-Alder cycloadducts in good yields.
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