Activation of Chiral (Salen)TiCl2 Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins

Chen Chen; Wen Biao Wu; Yan Hong Li; Qiu Hua Zhao; Jin Sheng Yu; Jian Zhou

doi:10.1021/acs.orglett.0c00612

Activation of Chiral (Salen)TiCl₂ Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins

Chen Chen
, Wen Biao Wu
, Yan Hong Li
, Qiu Hua Zhao
, Jin Sheng Yu
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

34 Scopus citations

Abstract

We report that phosphorane can activate (salen)TiCl₂ complex to achieve unprecedented excellent enantioselectivity and a broad substrate scope in the cyanation of nitroolefins. Our cyanating reagent Me₂(CH₂Cl)SiCN proves to be more active than TMSCN in this reaction, allowing 11 β-aliphatic nitrolefins and 12 β-CF₃ nitroolefins (either β-aryl or aliphatic) to work well to give the corresponding tertiary or quaternary β-nitronitriles with high to excellent enantioselectivity.

Original language	English
Pages (from-to)	2099-2104
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00612
State	Published - 6 Mar 2020

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title = "Activation of Chiral (Salen)TiCl2 Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins",

abstract = "We report that phosphorane can activate (salen)TiCl2 complex to achieve unprecedented excellent enantioselectivity and a broad substrate scope in the cyanation of nitroolefins. Our cyanating reagent Me2(CH2Cl)SiCN proves to be more active than TMSCN in this reaction, allowing 11 β-aliphatic nitrolefins and 12 β-CF3 nitroolefins (either β-aryl or aliphatic) to work well to give the corresponding tertiary or quaternary β-nitronitriles with high to excellent enantioselectivity.",

author = "Chen Chen and Wu, \{Wen Biao\} and Li, \{Yan Hong\} and Zhao, \{Qiu Hua\} and Yu, \{Jin Sheng\} and Jian Zhou",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "6",

doi = "10.1021/acs.orglett.0c00612",

language = "英语",

volume = "22",

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journal = "Organic Letters",

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T1 - Activation of Chiral (Salen)TiCl2 Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins

AU - Chen, Chen

AU - Wu, Wen Biao

AU - Li, Yan Hong

AU - Zhao, Qiu Hua

AU - Yu, Jin Sheng

AU - Zhou, Jian

PY - 2020/3/6

Y1 - 2020/3/6

N2 - We report that phosphorane can activate (salen)TiCl2 complex to achieve unprecedented excellent enantioselectivity and a broad substrate scope in the cyanation of nitroolefins. Our cyanating reagent Me2(CH2Cl)SiCN proves to be more active than TMSCN in this reaction, allowing 11 β-aliphatic nitrolefins and 12 β-CF3 nitroolefins (either β-aryl or aliphatic) to work well to give the corresponding tertiary or quaternary β-nitronitriles with high to excellent enantioselectivity.

AB - We report that phosphorane can activate (salen)TiCl2 complex to achieve unprecedented excellent enantioselectivity and a broad substrate scope in the cyanation of nitroolefins. Our cyanating reagent Me2(CH2Cl)SiCN proves to be more active than TMSCN in this reaction, allowing 11 β-aliphatic nitrolefins and 12 β-CF3 nitroolefins (either β-aryl or aliphatic) to work well to give the corresponding tertiary or quaternary β-nitronitriles with high to excellent enantioselectivity.

UR - https://www.scopus.com/pages/publications/85081945097

U2 - 10.1021/acs.orglett.0c00612

DO - 10.1021/acs.orglett.0c00612

M3 - 文章

C2 - 32105089

AN - SCOPUS:85081945097

SN - 1523-7060

VL - 22

SP - 2099

EP - 2104

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Activation of Chiral (Salen)TiCl₂ Complex by Phosphorane for the Highly Enantioselective Cyanation of Nitroolefins

Abstract

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