期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 10, 期 12, 页码 2737-2742出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201500764
关键词
asymmetric catalysis; chiral-at-metal; Diels-Alder; hydrocarbazoles; rhodium
资金
- National Natural Science Foundation of P. R. China [21472154, 21272192, 21201143]
- Program for Changjiang Scholars and Innovative Research Team of P. R. China (PCSIRT)
- National Thousand Talents Program of P. R. China
- 985 Program of the Chemistry and Chemical Engineering disciplines of Xiamen University
A bis-cyclometalated chiral-at-metal rhodium complex catalyzes the Diels-Alder reaction between N-Boc-protected 3-vinylindoles (Boc = tert-butyloxycarbonyl) and beta-carboxylic ester-substituted alpha,beta-unsaturated 2-acyl imidazoles with good-to-excellent regioselectivity (up to 99:1) and excellent diastereoselectivity (>50:1 d.r.) as well as enantioselectivity (92-99% ee) under optimized conditions. The rhodium catalyst serves as a chiral Lewis acid to activate the 2-acyl imidazole dienophile by two-point binding and overrules the preferred regioselectivity of the uncatalyzed reaction.
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