期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 144, 期 46, 页码 21022-21029出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c10863
关键词
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资金
- National Natural Science Foundation of China
- CAS Project for Young Scientists in Basic Research
- Fundamental Research Funds for the Central Universities
- [21971227]
- [22222113]
- [YSBR-054]
- [WK2340000090]
- [WK2340000111]
In this study, an efficient nickel-catalyzed reaction was reported for the synthesis of axially chiral 1,3-disubstituted allenes using newly designed diazo surrogates. The reaction showed broad substrate scope and excellent enantioselectivity, highlighting its potential for the synthesis of chiral compounds.
The general enantioselective catalytic synthesis of axially chiral 1,3-disubstituted allenes from readily available racemic propargylic alcohol derivatives remains a long-standing challenge in organic synthesis. Here we report an efficient nickel-catalyzed asymmetric propargylic substitution reaction/Myers rearrangement of racemic propargylic carbonates that furnishes a series of enantioenriched 1,3-disubstituted allenes using newly designed N-sulfonylhydrazone reagents as efficient diazo surrogates. This reaction proved to be remarkably general with regard to substrate scope, affording a diverse range of 1,3-disubstituted allenic compounds in good yields with excellent enantioselectivities. Additionally, applications of this powerful strategy for the enantioselective synthesis of methyl (S)-8-hydroxyocta-S,6-dienoate, (S)-laballenic acid, (S)-phlomic acid, and (S)-Delta(9,10)-pentacosadiene are described, further highlighting the broad potential of these new reagents for the discovery of novel reactions.
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