Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 51, Pages 18601-18607Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604003
Keywords
alkynes; cyclisation; enantioselectivity; halogenation; organocatalysis
Categories
Funding
- WWU Munster
- DFG [HE 6020/2-1, HE 6020/2-2, HE 6020/3-1]
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The cinchona alkaloid dimer (DHQD)(2)PHAL has been shown to be a broadly applicable catalyst for asymmetric halogenations. However, this catalyst does not have to be dimeric and a class of monomeric quinidine and quinine-derived catalysts was prepared, often showing superior selectivity in bromolactonisations of terminal alkynoic acids. Mechanistic investigations show that these organocatalysts act as host molecules that can bind carboxylic acid-based substrates as guests with substantial binding constants. Based on these findings, it is proposed that this class of catalysts is bifunctional in nature activating the halogenating agent as well as the nucleophile in electrophilic halogenation reactions.
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