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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

7 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8364-8369
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	45
DOIs	https://doi.org/10.1021/acs.orglett.2c03393
State	Published - 18 Nov 2022

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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.",

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

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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

Abstract

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