期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 46, 页码 20455-20458出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008952
关键词
chemoselectivity; contiguous stereogenic centers; diastereoselectivity; enantioselectivity; palladium
资金
- NSFC [21925109, 21772170]
- Outstanding Young Talents of Zhejiang Province High-level Personnel of Special Support [ZJWR0108]
- Fundamental Research Funds for the Central Universities [2018XZZX001-02]
The enantioselective desymmetrizing C-H activation of alpha-gem-dialkyl acyclic amides remains challenging because the availability of four chemically identical unbiased methylene C(sp(3))-H bonds and increased rotational freedoms of the acyclic systems add tremendous difficulties for chemo- and stereocontrol. We have developed a method for the synthesis of acyclic aliphatic amides with alpha,beta-contiguous stereogenic centers via Pd-II-catalyzed asymmetric arylation of unbiased methylene C(sp(3))-H, in good yields and with high levels of enantio-, chemo- and diastereoselectivity (up to >99 %eeand >20:1 d.r.). Successive application of this method enables the sequential arylation of thegem-dialkyl groups with two different aryl iodides, giving a range of beta-Ar-1-beta '-Ar-2-aliphatic acyclic amides containing three contiguous stereogenic centers with excellent diastereoselectivity.
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