Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade

Zhu, Dong-Xing1; Liu, Jian-Guo2,3; Xu, Ming-Hua2,3

2021-06-16

10.1021/jacs.1c03498

Journal of the American Chemical Society   影响因子和分区

0002-7863

1520-5126

A one-pot rhodium-catalyzed C-H functionalization/organocatalyzed oxa-Michael addition cascade reaction has been developed. This methodology enables the stereodivergent synthesis of diverse 2,3-disubstituted dihydrobenzofurans with broad functional group compatibility in good yields with high levels of stereoselectivity under exceptionally mild conditions. The full complement of stereoisomers of chiral 2,3-disubstituted dihydrobenzofurans and 3,4-disubstituted isochromans could be accessed at will by appropriate permutations of the two chiral catalysts. The current work provides a rare example of two chiral catalysts independently controlling two contiguous stereogenic centers subsequently via a two-step reaction in a single operation.

SCI ; EI

英语

NI论文

通讯

National Natural Science Foundation of China[21971103,21672229]

Chemistry

Chemistry, Multidisciplinary

WOS:000664300200012

AMER CHEMICAL SOC

20212610546247

Addition reactions ; Stereochemistry

Chemistry:801 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804

Web of Science

1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

Zhu, Dong-Xing,Liu, Jian-Guo,Xu, Ming-Hua. Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade[J]. Journal of the American Chemical Society,2021,143(23):8583-8589.

Zhu, Dong-Xing,Liu, Jian-Guo,&Xu, Ming-Hua.(2021).Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade.Journal of the American Chemical Society,143(23),8583-8589.

Zhu, Dong-Xing,et al."Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade".Journal of the American Chemical Society 143.23(2021):8583-8589.