A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines
1
Institut de Chimie des Substances Naturelles, CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette, France
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Publication type: Journal Article
Publication date: 1999-10-22
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Treatment of (2S)-1-O-benzylglycerol-2,3-bistriflate (2) with the trilithiated species of chiral building blocks 5−7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11−13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the cis isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60−72% overall yields.
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16
Total citations:
16
Citations from 2024:
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(12.5%)
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GOST
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Wang Q. et al. A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines // Journal of Organic Chemistry. 1999. Vol. 64. No. 23. pp. 8602-8607.
GOST all authors (up to 50)
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Wang Q., Sasaki N., Riche C., Potier P. A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines // Journal of Organic Chemistry. 1999. Vol. 64. No. 23. pp. 8602-8607.
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RIS
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TY - JOUR
DO - 10.1021/jo991052d
UR - https://doi.org/10.1021/jo991052d
TI - A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines
T2 - Journal of Organic Chemistry
AU - Wang, Qian
AU - Sasaki, N.André
AU - Riche, Claude
AU - Potier, Pierre
PY - 1999
DA - 1999/10/22
PB - American Chemical Society (ACS)
SP - 8602-8607
IS - 23
VL - 64
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1999_Wang,
author = {Qian Wang and N.André Sasaki and Claude Riche and Pierre Potier},
title = {A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines},
journal = {Journal of Organic Chemistry},
year = {1999},
volume = {64},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/jo991052d},
number = {23},
pages = {8602--8607},
doi = {10.1021/jo991052d}
}
Cite this
MLA
Copy
Wang, Qian, et al. “A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines.” Journal of Organic Chemistry, vol. 64, no. 23, Oct. 1999, pp. 8602-8607. https://doi.org/10.1021/jo991052d.