Tridentate Sulfoxide-N-olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution

Min Zhang; Jiteng Chen; Xiaolin Wang; Sheng Cai Zheng; Xiaoming Zhao

doi:10.1021/acs.orglett.4c00487

Tridentate Sulfoxide-N-olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution

Min Zhang
, Jiteng Chen
, Xiaolin Wang
, Sheng Cai Zheng^*
, Xiaoming Zhao^*

^*Corresponding author for this work

Tongji University

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A well-defined tridentate chiral sulfoxide-N-olefin ligand has been designed and applied in rhodium-catalyzed asymmetric allylic substitutions of racemic allylic carbonates, providing the branched allylic products in good yields with good to high enantioselectivities and excellent regioselectivities. This reaction mechanism, which involves the possible hemilability of olefin coordination on sulfoxide-N-olefin hybrid ligands with rhodium, is elaborated as well.

Original language	English
Pages (from-to)	1970-1974
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.4c00487
State	Published - 8 Mar 2024
Externally published	Yes

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10.1021/acs.orglett.4c00487

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title = "Tridentate Sulfoxide-N-olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution",

abstract = "A well-defined tridentate chiral sulfoxide-N-olefin ligand has been designed and applied in rhodium-catalyzed asymmetric allylic substitutions of racemic allylic carbonates, providing the branched allylic products in good yields with good to high enantioselectivities and excellent regioselectivities. This reaction mechanism, which involves the possible hemilability of olefin coordination on sulfoxide-N-olefin hybrid ligands with rhodium, is elaborated as well.",

author = "Min Zhang and Jiteng Chen and Xiaolin Wang and Zheng, \{Sheng Cai\} and Xiaoming Zhao",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

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doi = "10.1021/acs.orglett.4c00487",

language = "英语",

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journal = "Organic Letters",

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TY - JOUR

T1 - Tridentate Sulfoxide-N-olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution

AU - Zhang, Min

AU - Chen, Jiteng

AU - Wang, Xiaolin

AU - Zheng, Sheng Cai

AU - Zhao, Xiaoming

PY - 2024/3/8

Y1 - 2024/3/8

N2 - A well-defined tridentate chiral sulfoxide-N-olefin ligand has been designed and applied in rhodium-catalyzed asymmetric allylic substitutions of racemic allylic carbonates, providing the branched allylic products in good yields with good to high enantioselectivities and excellent regioselectivities. This reaction mechanism, which involves the possible hemilability of olefin coordination on sulfoxide-N-olefin hybrid ligands with rhodium, is elaborated as well.

AB - A well-defined tridentate chiral sulfoxide-N-olefin ligand has been designed and applied in rhodium-catalyzed asymmetric allylic substitutions of racemic allylic carbonates, providing the branched allylic products in good yields with good to high enantioselectivities and excellent regioselectivities. This reaction mechanism, which involves the possible hemilability of olefin coordination on sulfoxide-N-olefin hybrid ligands with rhodium, is elaborated as well.

UR - https://www.scopus.com/pages/publications/85186378027

U2 - 10.1021/acs.orglett.4c00487

DO - 10.1021/acs.orglett.4c00487

M3 - 文章

C2 - 38421216

AN - SCOPUS:85186378027

SN - 1523-7060

VL - 26

SP - 1970

EP - 1974

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Tridentate Sulfoxide-N-olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution

Abstract

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