Asymmetric synthesis of metallacarboranes using a traceless chiral auxiliary

Jiao Jiao; Pei He; Tilong Yang; Tingwei Zhang; Linghua Wang; Tian Han; Yong Nie; Zhenyang Lin; Pengfei Li

doi:10.1039/d3qo01528a

Asymmetric synthesis of metallacarboranes using a traceless chiral auxiliary

Jiao Jiao
, Pei He
, Tilong Yang
, Tingwei Zhang
, Linghua Wang
, Tian Han
, Yong Nie
, Zhenyang Lin
, Pengfei Li

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

2 Scopus citations

Abstract

An asymmetric synthesis of chiral metallacarboranes using a traceless chiral N-tertbutylsulfinamide auxiliary is reported. Investigations of the stereoselectivity and mechanism of the unprecedented formation of the metallacarboranes with a planar chiral nido-C₂B₉²⁻ ligand and an exo-polyhedral metal-substituted carbon stereocenter reveal a stereospecific S_N2-type reaction with a transition-metal nucleophile and an N-based leaving group. The findings may open a way for the preparation of chiral metallacarboranes and related compounds.

Original language	English
Pages (from-to)	5965-5970
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	10
Issue number	23
DOIs	https://doi.org/10.1039/d3qo01528a
State	Published - 26 Oct 2023

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title = "Asymmetric synthesis of metallacarboranes using a traceless chiral auxiliary",

abstract = "An asymmetric synthesis of chiral metallacarboranes using a traceless chiral N-tertbutylsulfinamide auxiliary is reported. Investigations of the stereoselectivity and mechanism of the unprecedented formation of the metallacarboranes with a planar chiral nido-C2B92− ligand and an exo-polyhedral metal-substituted carbon stereocenter reveal a stereospecific SN2-type reaction with a transition-metal nucleophile and an N-based leaving group. The findings may open a way for the preparation of chiral metallacarboranes and related compounds.",

author = "Jiao Jiao and Pei He and Tilong Yang and Tingwei Zhang and Linghua Wang and Tian Han and Yong Nie and Zhenyang Lin and Pengfei Li",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

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doi = "10.1039/d3qo01528a",

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TY - JOUR

T1 - Asymmetric synthesis of metallacarboranes using a traceless chiral auxiliary

AU - Jiao, Jiao

AU - He, Pei

AU - Yang, Tilong

AU - Zhang, Tingwei

AU - Wang, Linghua

AU - Han, Tian

AU - Nie, Yong

AU - Lin, Zhenyang

AU - Li, Pengfei

PY - 2023/10/26

Y1 - 2023/10/26

N2 - An asymmetric synthesis of chiral metallacarboranes using a traceless chiral N-tertbutylsulfinamide auxiliary is reported. Investigations of the stereoselectivity and mechanism of the unprecedented formation of the metallacarboranes with a planar chiral nido-C2B92− ligand and an exo-polyhedral metal-substituted carbon stereocenter reveal a stereospecific SN2-type reaction with a transition-metal nucleophile and an N-based leaving group. The findings may open a way for the preparation of chiral metallacarboranes and related compounds.

AB - An asymmetric synthesis of chiral metallacarboranes using a traceless chiral N-tertbutylsulfinamide auxiliary is reported. Investigations of the stereoselectivity and mechanism of the unprecedented formation of the metallacarboranes with a planar chiral nido-C2B92− ligand and an exo-polyhedral metal-substituted carbon stereocenter reveal a stereospecific SN2-type reaction with a transition-metal nucleophile and an N-based leaving group. The findings may open a way for the preparation of chiral metallacarboranes and related compounds.

UR - https://www.scopus.com/pages/publications/85175556854

U2 - 10.1039/d3qo01528a

DO - 10.1039/d3qo01528a

M3 - 文章

AN - SCOPUS:85175556854

SN - 2052-4110

VL - 10

SP - 5965

EP - 5970

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 23

ER -

Asymmetric synthesis of metallacarboranes using a traceless chiral auxiliary

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