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Synthesis 2023; 55(21): 3617-3624
DOI: 10.1055/a-2002-5931
special topic
C–H Bond Functionalization of Heterocycles

Rh(III)-Catalyzed Stereoselective C–H Homoallylation of Indolines with 4-Vinyl-1,3-dioxan-2-ones

Zhou Zhang
a   Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, P. R. of China
,
Jun-Jie Yi
a   Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, P. R. of China
,
Muhammad Aslam
a   Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, P. R. of China
,
Jie-Ping Wan∗
b   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China
,
Meng Sun∗
a   Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi’an 710127, P. R. of China
› Author AffiliationsWe are grateful to the National Natural Science Foundation of China (No. 21702160), Key Laboratory Research Foundation of Education Committee of Shaanxi Province (20JS145), Innovation Capability Support Program of Shaanxi (No. 2020TD-022), and the ‘Top-rated Discipline’ Construction Scheme of Shaanxi Higher Education for financial support.
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Abstract

An efficient and robust Rh(III)-catalyzed C–H homoallylation of indolines has been developed. Using 4-vinyl-1,3-dioxan-2-one as coupling partner, a range of homoallylic alcohols were prepared in excellent stereoselectivities. The current strategy features high efficiency, good yields, and exceptional functional group tolerance.

Key words

C–H homoallylation - Rh(III) catalysis - 4-vinyl-1,3-dioxan-2-ones - indoline - stereoselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2002-5931.
  • Supporting Information


Publication History

Received: 18 November 2022

Accepted after revision: 21 December 2022

Accepted Manuscript online:
21 December 2022

Article published online:
16 January 2023

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