Me2(CH2Cl)SiCF3Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group

Chuan Wen Lei; Xi Yu Wang; Bo Shuai Mu; Jin Sheng Yu; Ying Zhou; Jian Zhou

doi:10.1021/acs.orglett.2c03393

Me₂(CH₂Cl)SiCF₃Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group

Chuan Wen Lei
, Xi Yu Wang
, Bo Shuai Mu
, Jin Sheng Yu^*
, Ying Zhou^*
, Jian Zhou^*

^*此作品的通讯作者

化学与分子工程学院

Guizhou University of Traditional Chinese Medicine
East China Normal University
CAS - Shanghai Institute of Organic Chemistry

科研成果: 期刊稿件 › 文章 › 同行评审

8 引用（Scopus）

摘要

An unprecedented tandem trifluoromethylsilylation/intramolecular S_N2 substitution sequence was realized by using bifunctional reagent Me₂(CH₂Cl)SiCF₃, allowing efficient construction of valuable trifluoromethylated oxasilacyclohexanes that are difficult to access by known methods. Initial attempts into developing asymmetric variant reveal that using cinchonine-derived dimeric PTC catalyst could afford chiral oxasilacyclohexanes in up to 92% enantiomeric excess.

源语言	英语
页（从-至）	8364-8369
页数	6
期刊	Organic Letters
卷	24
期	45
DOI	https://doi.org/10.1021/acs.orglett.2c03393
出版状态	已出版 - 18 11月 2022

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10.1021/acs.orglett.2c03393

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title = "Me2(CH2Cl)SiCF3Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group",

abstract = "An unprecedented tandem trifluoromethylsilylation/intramolecular SN2 substitution sequence was realized by using bifunctional reagent Me2(CH2Cl)SiCF3, allowing efficient construction of valuable trifluoromethylated oxasilacyclohexanes that are difficult to access by known methods. Initial attempts into developing asymmetric variant reveal that using cinchonine-derived dimeric PTC catalyst could afford chiral oxasilacyclohexanes in up to 92\% enantiomeric excess.",

author = "Lei, \{Chuan Wen\} and Wang, \{Xi Yu\} and Mu, \{Bo Shuai\} and Yu, \{Jin Sheng\} and Ying Zhou and Jian Zhou",

year = "2022",

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doi = "10.1021/acs.orglett.2c03393",

language = "英语",

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pages = "8364--8369",

journal = "Organic Letters",

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T1 - Me2(CH2Cl)SiCF3Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group

AU - Lei, Chuan Wen

AU - Wang, Xi Yu

AU - Mu, Bo Shuai

AU - Yu, Jin Sheng

AU - Zhou, Ying

AU - Zhou, Jian

PY - 2022/11/18

Y1 - 2022/11/18

N2 - An unprecedented tandem trifluoromethylsilylation/intramolecular SN2 substitution sequence was realized by using bifunctional reagent Me2(CH2Cl)SiCF3, allowing efficient construction of valuable trifluoromethylated oxasilacyclohexanes that are difficult to access by known methods. Initial attempts into developing asymmetric variant reveal that using cinchonine-derived dimeric PTC catalyst could afford chiral oxasilacyclohexanes in up to 92% enantiomeric excess.

AB - An unprecedented tandem trifluoromethylsilylation/intramolecular SN2 substitution sequence was realized by using bifunctional reagent Me2(CH2Cl)SiCF3, allowing efficient construction of valuable trifluoromethylated oxasilacyclohexanes that are difficult to access by known methods. Initial attempts into developing asymmetric variant reveal that using cinchonine-derived dimeric PTC catalyst could afford chiral oxasilacyclohexanes in up to 92% enantiomeric excess.

UR - https://www.scopus.com/pages/publications/85141719390

U2 - 10.1021/acs.orglett.2c03393

DO - 10.1021/acs.orglett.2c03393

M3 - 文章

C2 - 36318643

AN - SCOPUS:85141719390

SN - 1523-7060

VL - 24

SP - 8364

EP - 8369

JO - Organic Letters

JF - Organic Letters

IS - 45

ER -

Me2(CH2Cl)SiCF3Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group

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Me₂(CH₂Cl)SiCF₃Facilitated Tandem Synthesis of Oxasilacycles Featuring a Trifluoromethyl Group