期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 19, 页码 6900-6903出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja503117q
关键词
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资金
- National Natural Sciences Foundation of China [21121062, 20932008, 21272250]
- Chinese Academy of Sciences
- U.S. National Science Foundation [CHE-1059084]
- Direct For Mathematical & Physical Scien [1361104, 1059084] Funding Source: National Science Foundation
- Division Of Chemistry [1361104, 1059084] Funding Source: National Science Foundation
Stereocontrol in the synthesis of structurally complex molecules, especially those with all-carbon quaternary stereocenters, remains a challenge. Here, we reported the preparation of a class of tetracyclic cyclopenta-fused spiroindoline skeletons through Cu(II)catalyzed intramolecular [3 + 2] annulation reactions of donor-acceptor cyclopropanes with indoles. Both cis- and trans-diastereomers of tetracyclic spiroindolines are accessed with high selectivities by altering the remote ester groups of cyclopropanes. The origins of this stereocontrol are identified using DFT calculations: attractive interactions between the ester group and arene favor the generation of the trans isomer, while the formation of the cis isomer is preferred when steric repulsions become predominant.
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