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

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2714-2718
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.163
Publication status	Published - 21 Apr 2008

Keywords

Acetal
Acetate
Acetonide
Homogeneous catalysis
Protecting groups

Access to Document

10.1016/j.tetlet.2008.02.163

Cite this

@article{e67918c5124a434d9fb28d0fd3bd3ab5,

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",

volume = "49",

pages = "2714--2718",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "17",

}

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this