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Publication details

Document type
Journal articles

Document subtype
Full paper

Title
Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety

Participants in the publication
V. Cachatra (Author)
A.Almeida (Author)
Dep. Química e Bioquímica
 J. Sardinha (Author)
S. D. Lucas (Author)
A. Gomes (Author)
P. D. Vaz (Author)
M. H. Florêncio (Author)
Dep. Química e Bioquímica
 CQB
 R.Nunes (Author)
Dep. Química e Bioquímica
 BioISI
 CQB
 D. Vila-Viçosa (Author)
Dep. Química e Bioquímica
 CQB
 M. J. Calhorda (Author)
Dep. Química e Bioquímica
 CQB
 A. P. Rauter (Author)
Dep. Química e Bioquímica
 CQB
Summary
2-O-Acyl protected-D-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to a?ord regio- and stereoselectively 2-(Z)-alkenes in 10−60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3ulose to enol, acyl migration, tautomerization to the 3-O-acyl2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-ole?nation of 2-O-pivaloyl-3-uloses gave (E)alkenes, key precursors for the miharamycins’ bicyclic sugar moiety.

Date of Submisson/Request
2015-10-01
Date of Publication
2015-11-09

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
ORGANIC LETTERS

Publication Identifiers
ISSN - 1523-7060

Publisher
American Chemical Society (ACS)

Volume
17

Number of pages
4
Starting page
5622
Last page
5625

Document Identifiers
URL - http://dx.doi.org/10.1021/acs.orglett.5b02849
DOI - https://doi.org/10.1021/acs.orglett.5b02849

Rankings
Web Of Science Q1 (2015) - 6.732 - Chemistry, Organic
SCIMAGO Q1 (2015) - 3.005 - Biochemistry
SCIMAGO Q1 (2015) - 3.005 - Organic Chemistry
SCIMAGO Q1 (2015) - 3.005 - Physical and Theoretical Chemistry

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APA
V. Cachatra, A.Almeida, J. Sardinha, S. D. Lucas, A. Gomes, P. D. Vaz, M. H. Florêncio, R.Nunes, D. Vila-Viçosa, M. J. Calhorda, A. P. Rauter, (2015). Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety. ORGANIC LETTERS, 17, 5622-5625. ISSN 1523-7060. eISSN . http://dx.doi.org/10.1021/acs.orglett.5b02849

IEEE
V. Cachatra, A.Almeida, J. Sardinha, S. D. Lucas, A. Gomes, P. D. Vaz, M. H. Florêncio, R.Nunes, D. Vila-Viçosa, M. J. Calhorda, A. P. Rauter, "Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety" in ORGANIC LETTERS, vol. 17, pp. 5622-5625, 2015. 10.1021/acs.orglett.5b02849

BIBTEX
@article{26545, author = {V. Cachatra and A.Almeida and J. Sardinha and S. D. Lucas and A. Gomes and P. D. Vaz and M. H. Florêncio and R.Nunes and D. Vila-Viçosa and M. J. Calhorda and A. P. Rauter}, title = {Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety}, journal = {ORGANIC LETTERS}, year = 2015, pages = {5622-5625}, volume = 17 }