Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents
Publication type: Journal Article
Publication date: 2004-11-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
15549811
Organic Chemistry
Abstract
beta,beta-Disubstituted chiral vinylic sulfoxides bearing functionalities have been synthesized via Cu-catalyzed conjugate addition of organozinc reagents to chiral 1-alkynyl sulfoxides. Due to the availability of functionalized organozinc reagents and high syn-selectivity of the reaction, both geometric beta,beta-disubstituted vinylic sulfoxides were selectively synthesized. Furthermore, 1-alkynyl sulfoxides were derivatized into trisubstituted vinylic sulfoxides by trapping the resulting alpha-sulfinyl vinylic carbanion with electrophiles. Highly diastereoselective THF and THP ring formations were accomplished by means of this methodology followed by an intramolecular Michael addition.
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31
Total citations:
31
Citations from 2024:
2
(6%)
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GOST
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Maezaki N. et al. Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents // Journal of Organic Chemistry. 2004. Vol. 69. No. 24. pp. 8387-8393.
GOST all authors (up to 50)
Copy
Maezaki N., Sawamoto H., Suzuki T., Yoshigami R., Tanaka T. Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents // Journal of Organic Chemistry. 2004. Vol. 69. No. 24. pp. 8387-8393.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo048747l
UR - https://doi.org/10.1021/jo048747l
TI - Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents
T2 - Journal of Organic Chemistry
AU - Maezaki, Naoyoshi
AU - Sawamoto, Hiroaki
AU - Suzuki, Tomoko
AU - Yoshigami, Ryoko
AU - Tanaka, Tetsuaki
PY - 2004
DA - 2004/11/01
PB - American Chemical Society (ACS)
SP - 8387-8393
IS - 24
VL - 69
PMID - 15549811
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2004_Maezaki,
author = {Naoyoshi Maezaki and Hiroaki Sawamoto and Tomoko Suzuki and Ryoko Yoshigami and Tetsuaki Tanaka},
title = {Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents},
journal = {Journal of Organic Chemistry},
year = {2004},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jo048747l},
number = {24},
pages = {8387--8393},
doi = {10.1021/jo048747l}
}
Cite this
MLA
Copy
Maezaki, Naoyoshi, et al. “Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents.” Journal of Organic Chemistry, vol. 69, no. 24, Nov. 2004, pp. 8387-8393. https://doi.org/10.1021/jo048747l.