A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O

Qin Pei Wu; Ming Xin Zhou; Xiao Dong Xi; Di Song; Yuan Wang; Hai Xia Liu; Yun Zheng Li; Qing Shan Zhang

doi:10.1016/j.tetlet.2008.02.163

A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)₃·xH₂O

Qin Pei Wu^*, Ming Xin Zhou, Xiao Dong Xi, Di Song, Yuan Wang, Hai Xia Liu, Yun Zheng Li, Qing Shan Zhang

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

16 引用（Scopus）

摘要

The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)₃·xH₂O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides could be tunably converted into 2-acetoxyisopropyl or diacetate groups.

源语言	英语
页（从-至）	2714-2718
页数	5
期刊	Tetrahedron Letters
卷	49
期	17
DOI	https://doi.org/10.1016/j.tetlet.2008.02.163
出版状态	已出版 - 21 4月 2008

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10.1016/j.tetlet.2008.02.163

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title = "A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O",

abstract = "The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides could be tunably converted into 2-acetoxyisopropyl or diacetate groups.",

keywords = "Acetal, Acetate, Acetonide, Homogeneous catalysis, Protecting groups",

author = "Wu, {Qin Pei} and Zhou, {Ming Xin} and Xi, {Xiao Dong} and Di Song and Yuan Wang and Liu, {Hai Xia} and Li, {Yun Zheng} and Zhang, {Qing Shan}",

year = "2008",

month = apr,

day = "21",

doi = "10.1016/j.tetlet.2008.02.163",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O

AU - Wu, Qin Pei

AU - Zhou, Ming Xin

AU - Xi, Xiao Dong

AU - Song, Di

AU - Wang, Yuan

AU - Liu, Hai Xia

AU - Li, Yun Zheng

AU - Zhang, Qing Shan

PY - 2008/4/21

Y1 - 2008/4/21

N2 - The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides could be tunably converted into 2-acetoxyisopropyl or diacetate groups.

AB - The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides could be tunably converted into 2-acetoxyisopropyl or diacetate groups.

KW - Acetal

KW - Acetate

KW - Acetonide

KW - Homogeneous catalysis

KW - Protecting groups

UR - http://www.scopus.com/inward/record.url?scp=40949125536&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.02.163

DO - 10.1016/j.tetlet.2008.02.163

M3 - Article

AN - SCOPUS:40949125536

SN - 0040-4039

VL - 49

SP - 2714

EP - 2718

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O

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A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)₃·xH₂O