Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies

doi:10.1038/s41467-020-19294-8

	Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies
	Wang, Jiawen1,2 ; Zheng, Sujuan 3; Rajkumar, Subramani1 ; Xie, Jinglei 1; Yu, Na1 ; Peng, Qian 3; Yang, Xiaoyu1
	2020-11-02
发表期刊	NATURE COMMUNICATIONS (IF:14.7[JCR-2023],16.1[5-Year])
ISSN	2041-1723
卷号	11 期号:1 页码:#VALUE!
DOI	10.1038/s41467-020-19294-8
摘要	Chiral molecules with multiple stereocenters are widely present in natural products and pharmaceuticals, whose absolute and relative configurations are both critically important for their physiological activities. In spite of the fact that a series of ingenious strategies have been developed for asymmetric diastereodivergent catalysis, most of these methods are limited to the divergent construction of point chirality. Here we report an enantioselective and diastereodivergent synthesis of trisubstituted allenes by asymmetric additions of oxazolones to activated 1,3-enynes enabled by chiral phosphoric acid (CPA) catalysis, where the divergence of the allenic axial stereogenicity is realized by modifications of CPA catalysts. Density functional theory (DFT) calculations are performed to elucidate the origin of diastereodivergence by the stacking- and stagger-form in the transition state (TS) of allene formation step, as well as to disclose a Munchnone-type activation mode of oxazolones under Bronsted acid catalysis.
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收录类别	SCI ; SCIE
语种	英语
WOS研究方向	Science & Technology - Other Topics
WOS类目	Multidisciplinary Sciences
WOS记录号	WOS:000617729200004
出版者	NATURE RESEARCH
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/125979
专题	物质科学与技术学院_硕士生物质科学与技术学院_PI研究组_杨晓瑜组物质科学与技术学院_公共科研平台_分析测试平台
通讯作者	Peng, Qian; Yang, Xiaoyu
作者单位	1.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China; 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China; 3.Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
第一作者单位	物质科学与技术学院
通讯作者单位	物质科学与技术学院
第一作者的第一单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Wang, Jiawen,Zheng, Sujuan,Rajkumar, Subramani,et al. Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies[J]. NATURE COMMUNICATIONS,2020,11(1):#VALUE!.
APA	Wang, Jiawen.,Zheng, Sujuan.,Rajkumar, Subramani.,Xie, Jinglei.,Yu, Na.,...&Yang, Xiaoyu.(2020).Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies.NATURE COMMUNICATIONS,11(1),#VALUE!.
MLA	Wang, Jiawen,et al."Chiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies".NATURE COMMUNICATIONS 11.1(2020):#VALUE!.