Stereoselective C-Glycosylation Reactions with Arylzinc Reagents
Sébastien Lemaire
1
,
Ioannis N Houpis
1
,
Tingting Xiao
1
,
Juanjuan Li
1
,
Eric Digard
1
,
Charlotte Gozlan
1
,
Renmao Liu
1
,
Andrey Gavryushin
1
,
Coura Diène
1
,
Youchu Wang
1
,
Vittorio Farina
1
,
Paul Knochel
1
1
Pharmaceutical Development and Manufacturing Sciences, Janssen Pharmaceutica, Turnhoutseweg 30, B-2340 Beerse, Belgium, Department Chemie und Biochemie, Ludwig-Maximilian Universität München, Butenandtstrasse 5-12, Haus F, 81377 München, Germany, and WuxiApptec, Process Chemistry, 288 Fute Zhong road, Shanghai 200131, People’s Republic of China
|
Publication type: Journal Article
Publication date: 2012-03-02
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
22385274
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A general, transition-metal-free, highly stereoselective cross-coupling reaction between glycosyl bromides and various arylzinc reagents leading to β-arylated glycosides is reported. The stereoselectivity of the reaction is explained by invoking anchimeric assistance via a bicyclic intermediate. Stereochemical probes confirm the participation of the 2-pivaloyloxy group. Finally, this new method was applied to a short and efficient stereoselective synthesis of Dapagliflozin and Canagliflozin.
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126
Total citations:
126
Citations from 2024:
21
(16.66%)
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GOST
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Lemaire S. et al. Stereoselective C-Glycosylation Reactions with Arylzinc Reagents // Organic Letters. 2012. Vol. 14. No. 6. pp. 1480-1483.
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Lemaire S., Houpis I. N., Xiao T., Li J., Digard E., Gozlan C., Liu R., Gavryushin A., Diène C., Wang Y., Farina V., Knochel P. Stereoselective C-Glycosylation Reactions with Arylzinc Reagents // Organic Letters. 2012. Vol. 14. No. 6. pp. 1480-1483.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol300220p
UR - https://doi.org/10.1021/ol300220p
TI - Stereoselective C-Glycosylation Reactions with Arylzinc Reagents
T2 - Organic Letters
AU - Lemaire, Sébastien
AU - Houpis, Ioannis N
AU - Xiao, Tingting
AU - Li, Juanjuan
AU - Digard, Eric
AU - Gozlan, Charlotte
AU - Liu, Renmao
AU - Gavryushin, Andrey
AU - Diène, Coura
AU - Wang, Youchu
AU - Farina, Vittorio
AU - Knochel, Paul
PY - 2012
DA - 2012/03/02
PB - American Chemical Society (ACS)
SP - 1480-1483
IS - 6
VL - 14
PMID - 22385274
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2012_Lemaire,
author = {Sébastien Lemaire and Ioannis N Houpis and Tingting Xiao and Juanjuan Li and Eric Digard and Charlotte Gozlan and Renmao Liu and Andrey Gavryushin and Coura Diène and Youchu Wang and Vittorio Farina and Paul Knochel},
title = {Stereoselective C-Glycosylation Reactions with Arylzinc Reagents},
journal = {Organic Letters},
year = {2012},
volume = {14},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ol300220p},
number = {6},
pages = {1480--1483},
doi = {10.1021/ol300220p}
}
Cite this
MLA
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Lemaire, Sébastien, et al. “Stereoselective C-Glycosylation Reactions with Arylzinc Reagents.” Organic Letters, vol. 14, no. 6, Mar. 2012, pp. 1480-1483. https://doi.org/10.1021/ol300220p.