Highly efficient, regio- and stereoselective ring opening of epoxides and thiiranes with Ce(OTf)4

Article abstract of DOI:10.1080/00397919808005728

Ceric triflate, Ce(OTf)₄ is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation to the corresponding disulfides occur efficiently in the presence of this reagent. A mild method for the preparation of dithianes from thiiranes and Ce(OTf)₄ is also described.

Full text of DOI:10.1080/00397919808005728

This article was downloaded by: [Harvard College]
On: 25 June 2013, At: 21:50
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number:
1072954 Registered office: Mortimer House, 37-41 Mortimer Street,
London W1T 3JH, UK
Synthetic Communications:
An International Journal
for Rapid Communication of
Synthetic Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
Highly Efficient, Regio-
and Stereoselective Ring
Opening of Epoxides and
Thiiranes with Ce(OTf)4
N. Iranpoor a , M. Shekarriz a & F. Shiriny a
a Chemistry Department , Shiraz University ,
Shiraz , 71454 , Iran
Published online: 21 Aug 2006.
To cite this article: N. Iranpoor , M. Shekarriz & F. Shiriny (1998): Highly
Efficient, Regio- and Stereoselective Ring Opening of Epoxides and Thiiranes
with Ce(OTf)4 , Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 28:2, 347-366
To link to this article: http://dx.doi.org/10.1080/00397919808005728
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/
terms-and-conditions
This article may be used for research, teaching, and private study
purposes. Any substantial or systematic reproduction, redistribution,
reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden.

The publisher does not give any warranty express or implied or make
any representation that the contents will be complete or accurate or
up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher
shall not be liable for any loss, actions, claims, proceedings, demand, or
costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.