Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis

doi:10.1021/acscatal.3c02851

	Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis
	Shen, Guosong; He, Faqian; Xie, Wansen; Gu, Huanchao; Yang, Xiaoyu
	2023-09-08
发表期刊	ACS CATALYSIS (IF:11.3[JCR-2023],12.6[5-Year])
ISSN	2155-5435
EISSN	2155-5435
卷号	13 期号:19 页码:12472-12480
发表状态	已发表
DOI	10.1021/acscatal.3c02851
摘要	Asymmetric diastereodivergent catalysis is a powerful strategy for accessing different stereoisomers of a molecule, which are important in the discovery of biologically and pharmacologically active candidates. While the asymmetric diastereodivergent synthesis of acyclic molecules has seen recent rapid development, the corresponding asymmetric diastereodivergent cycloaddition reactions have received comparatively less attention. Herein, we report the asymmetric diastereodivergent synthesis of chromanes with C2,C3-contiguous tetrasubstituted stereocenters via chiral phosphoric acid (CPA)-catalyzed [4 + 2] cycloadditions of ortho-quinone methides with ?-silyl-substituted allenones. A wide range of C3-epimeric chromanes were generated with high to excellent diastereoselectivities and enantioselectivities, starting from the same substrates but with modifications of the CPA catalysts. The diverse derivatizations of these chiral chromane stereoisomers into complex scaffolds illustrate the utility and value of this method.
关键词	asymmetric [4+2] cycloaddition diastereodivergent chromanes ortho-quinone methides chiral phosphoric acids
URL	查看原文
收录类别	EI ; SCI
语种	英语
资助项目	NSFC["22222107","22171186"] ; Analytical Instrumentation Center[SPST-AIC10112914]
WOS研究方向	Chemistry
WOS类目	Chemistry, Physical
WOS记录号	WOS:001065402400001
出版者	AMER CHEMICAL SOC
EI入藏号	20234014833560
EI主题词	Synthesis (chemical)
EI分类号	405.1 Construction Equipment ; 801 Chemistry ; 802.2 Chemical Reactions ; 804.1 Organic Compounds ; 804.2 Inorganic Compounds ; 931.3 Atomic and Molecular Physics
原始文献类型	Journal article (JA)
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/329038
专题	物质科学与技术学院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_博士生
通讯作者	Yang, Xiaoyu
作者单位	ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, 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	Shen, Guosong,He, Faqian,Xie, Wansen,et al. Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis[J]. ACS CATALYSIS,2023,13(19):12472-12480.
APA	Shen, Guosong,He, Faqian,Xie, Wansen,Gu, Huanchao,&Yang, Xiaoyu.(2023).Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis.ACS CATALYSIS,13(19),12472-12480.
MLA	Shen, Guosong,et al."Diastereodivergent Asymmetric [4 + 2] Cycloaddition of In Situ Generated ortho-Quinone Methides and Allenyl Ketones Enabled by Chiral Phosphoric Acid Catalysis".ACS CATALYSIS 13.19(2023):12472-12480.