期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 4, 页码 1158-1162出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812344
关键词
cyclizations; heterocycles; organocatalysis; reaction mechanisms; synthetic methods
资金
- National Key Research and Development Program of China [2016YFA0202900]
- National Basic Research Program of China [2015CB856600]
- NSFC [21332009, 21772219, 91856201]
- Science and Technology Commission of Shanghai Municipality [16XD1404300, 18QA1404900, 16490712200]
- CAS [XDB20000000, QYZDYSSWSLH012]
- CAS (Youth Innovation Promotion Association) [2017302]
By manipulating the reactivity of spiroindolenine species, a sequential Michael/retro-Mannich/Mannich reaction of omega-indol-3-yl alpha,beta-unsaturated ketones was developed. In the presence of 10 mol % of a chiral phosphoric acid as the catalyst, a series of 3-(indol-3-yl)-pyrrolidines were synthesized in high yields (up to 91 %) with excellent stereoselectivities (up to 92 % ee, >19:1 d.r.). The products obtained here undergo diverse functional-group transformations. The mechanistic proposal of this reaction is supported by DFT calculations.
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