期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 44, 页码 15778-15782出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910183
关键词
chirality; cyclizations; desymmetrization; N-heterocyclic carbenes; synthetic methods
资金
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003, MOE2016-T2-1-032, RG108/16]
- A* STAR Individual Research Grant [A1783c0008]
- Nanyang Research Award Grant, Nanyang Technological University
- Guizhou Province First-Class Disciplines Project (Yiliu Xueke Jianshe Xiangmu)-GNYL [(2017) 008]
- Guizhou University of Traditional Chinese Medicine (China)
- National Natural Science Foundation of China [21772029, 21472028]
- National Key Technologies RD Program [2014BAD23B01]
- 10 Talent Plan (Shicengci) of Guizhou Province [[2016] 5649]
- Guizhou Province Returned Overseas Student Science and Technology Activity Program [(2014)-2]
- Science and Technology Department of Guizhou Province [[2018] 2802, [2019] 1020]
- Guizhou University
Multisubstituted arenes such as indanes with attached all-carbon quaternary centers are unique scaffolds in synthetic functional molecules and sophisticated natural products. A key challenge in preparing such molecules lies in the enantioselective installation of the quaternary carbon centers. Conventional methods in this direction include asymmetric substitution reactions and substrate-controlled cyclization reactions. These reactions lead to poor stereoselectivities and/or require long and tedious synthetic steps. Disclosed here is a one-step organic catalytic strategy for enantioselective access to this class of molecules. The reaction involves an N-heterocyclic carbene catalyzed process for direct benzene construction, indane formation, remote-carbon desymmetrization, and excellent chirality control. This approach will enable the concise synthesis of arene-containing molecules, including those with complex structures and challenging chiral centers.
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