期刊
ACS CATALYSIS
卷 9, 期 3, 页码 1956-1961出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04870
关键词
five-membered heteroatropisomers; palladium; atroposelective; C-H alkynylation; rotational barrier
资金
- NSFC [21772170, 21572201, 21702182, 21873081]
- National Basic Research Program of China [2015CB856600]
- Fundamental Research Funds for the Central Universities [2018XZZX001-02]
- Zhejiang Provincial NSFC [LR17B020001]
Due to the lower rotational barriers, the catalytic asymmetric construction of atropisomeric species featuring a five-membered ring remains a formidable challenge. Herein, we describe a Pd-catalyzed atroposelective C-H alkynylation to synthesize such atropisomers. A wide range of atropisomers displaying either a stereogenic C-N or C-C bond featuring one or even two five-membered rings were obtained (up to 98% yield and up to >99% ee). Various five-membered heteroarenes, including pyrroles, thiophenes, benzothiophenes, and benzofurans were compatible with this protocol. Notably, this strategy offers the catalytic asymmetric synthesis of axially chiral 3,3'-bisbenzothiophene with good ee (93% ee). Computational studies revealed the key structural elements that differentiate the rotational barriers of benzothiophene and benzofuran moieties.
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