Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis
Тип публикации: Journal Article
Дата публикации: 2019-10-24
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SJR: 0.604
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31646859
Organic Chemistry
Краткое описание
Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3.
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Gudmundsson H. G. et al. Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 22. pp. 14868-14882.
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Gudmundsson H. G., Kuper C. J., Bonnete F., Urbitsch F., Elbert B. L., ANDERSON E. Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis // Journal of Organic Chemistry. 2019. Vol. 84. No. 22. pp. 14868-14882.
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TY - JOUR
DO - 10.1021/acs.joc.9b01664
UR - https://doi.org/10.1021/acs.joc.9b01664
TI - Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis
T2 - Journal of Organic Chemistry
AU - Gudmundsson, Haraldur G
AU - Kuper, Christian J
AU - Bonnete, F.
AU - Urbitsch, Felix
AU - Elbert, Bryony L
AU - ANDERSON, EDWARD F.
PY - 2019
DA - 2019/10/24
PB - American Chemical Society (ACS)
SP - 14868-14882
IS - 22
VL - 84
PMID - 31646859
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2019_Gudmundsson,
author = {Haraldur G Gudmundsson and Christian J Kuper and F. Bonnete and Felix Urbitsch and Bryony L Elbert and EDWARD F. ANDERSON},
title = {Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.9b01664},
number = {22},
pages = {14868--14882},
doi = {10.1021/acs.joc.9b01664}
}
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Gudmundsson, Haraldur G., et al. “Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis.” Journal of Organic Chemistry, vol. 84, no. 22, Oct. 2019, pp. 14868-14882. https://doi.org/10.1021/acs.joc.9b01664.
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