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Efficient Synthesis of Photolabile Alkoxy Benzoin Protecting Groups

Stowell, Michael H. B. and Rock, Ronald S. and Rees, D. C. and Chan, Sunney I. (1996) Efficient Synthesis of Photolabile Alkoxy Benzoin Protecting Groups. Tetrahedron Letters, 37 (3). pp. 307-310. ISSN 0040-4039. http://resolver.caltech.edu/CaltechAUTHORS:20150205-140522838

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Abstract

An effective implementation of the Corey-Seebach dithiane addition for the synthesis of photolabile alkoxy benzoin adducts is reported. The method allows for the facile synthesis of photolabile 3′,5′-dimethoxybenzoin protected compounds in near quantitative yield and is general in that it can be used for the synthesis of both symmetrical and unsymmetrical benzoins. Importantly, the dithiane intermediate reported is a versatile starting material for the synthesis of many photolabile compounds and should serve as a useful protecting group in complex synthetic schemes requiring multiple orthogonal protecting groups.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/0040-4039(95)02159-0 DOIArticle
http://www.sciencedirect.com/science/article/pii/0040403995021590PublisherArticle
ORCID:
AuthorORCID
Rees, D. C.0000-0002-1076-1503
Chan, Sunney I.0000-0002-5348-2723
Contact Email Address:phoebe@caltech.edu
Additional Information:© 1996 Elsevier Science Ltd. Received in USA 7 September 1995; revised 7 November 1995; accepted 10 November 1995. We thank Prof. E. M. Carreira for helpful discussions and critical reading of this manuscript. This work was supported by NIH grant GM 22432 from the National Institute of General Medical Sciences, U.S. Public Health Service. Contribution number 9139.
Funders:
Funding AgencyGrant Number
NIHGM 22432
National Institute of General Medical SciencesUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Arthur Amos Noyes Laboratory9139
Record Number:CaltechAUTHORS:20150205-140522838
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150205-140522838
Official Citation:Michael H.B. Stowell, Ronald S. Rock, D.C. Rees, Sunney I. Chan, Efficient synthesis of photolabile alkoxy benzoin protecting groups, Tetrahedron Letters, Volume 37, Issue 3, 15 January 1996, Pages 307-310, ISSN 0040-4039, http://dx.doi.org/10.1016/0040-4039(95)02159-0. (http://www.sciencedirect.com/science/article/pii/0040403995021590)
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ID Code:54437
Collection:CaltechAUTHORS
Deposited By: SWORD User
Deposited On:08 Feb 2015 03:08
Last Modified:22 Sep 2017 04:50

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