том 87 издание 23

Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles

Тип публикацииJournal Article
Дата публикации2022-11-10
SCImago Q2
WOS Q1
БС1
SJR0.604
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Краткое описание
A convenient and efficient synthetic strategy to prepare enantioenriched gem-difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles is described. Fluoride-mediated diastereoselective nucleophilic addition of PhSCF2SiMe3 to chiral N-tert-butanesulfinyl ketimines derived from isatins was a key step and provided diastereomeric adducts, which were readily separable. Removal of the chiral sulfinyl group followed by structural manipulation afforded chiral gem-difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles.
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Keereewan S. et al. Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles // Journal of Organic Chemistry. 2022. Vol. 87. No. 23.
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Keereewan S., Kuhakarn C., Leowanawat P., Saithong S., Reutrakul V., Soorukram D. Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles // Journal of Organic Chemistry. 2022. Vol. 87. No. 23.
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TY - JOUR
DO - 10.1021/acs.joc.2c02098
UR - https://doi.org/10.1021/acs.joc.2c02098
TI - Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles
T2 - Journal of Organic Chemistry
AU - Keereewan, Sirisuk
AU - Kuhakarn, Chutima
AU - Leowanawat, Pawaret
AU - Saithong, Saowanit
AU - Reutrakul, Vichai
AU - Soorukram, Darunee
PY - 2022
DA - 2022/11/10
PB - American Chemical Society (ACS)
IS - 23
VL - 87
PMID - 36366856
SN - 0022-3263
SN - 1520-6904
ER -
BibTex
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@article{2022_Keereewan,
author = {Sirisuk Keereewan and Chutima Kuhakarn and Pawaret Leowanawat and Saowanit Saithong and Vichai Reutrakul and Darunee Soorukram},
title = {Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.2c02098},
number = {23},
doi = {10.1021/acs.joc.2c02098}
}
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