Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes
Тип публикации: Journal Article
Дата публикации: 2017-12-14
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
29239616
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
GaCl3 and (IPr)GaCl3/AgSbF6 formed γ-tertiary and γ-quaternary carbons via homoconjugate addition of organoboron nucleophiles to diester- and ketone-functionalized cyclopropanes. Electron donor group cyclopropane substituents were not needed, allowing electron-deficient aryl, alkenyl, alkyl, and hydrogen-substituted cyclopropanes to be used. The catalytic conditions were compatible with alkenyl, alkynyl, and aryl nucleophiles, including ortho-substituted aromatics, to synthesize highly hindered quaternary carbons. Alkynyl nucleophiles formed substituted cyclopentenes. A control experiment supports an intermediate carbocation in quaternary carbon center formation.
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Nguyen T. N., May J. A. Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes // Organic Letters. 2017. Vol. 20. No. 1. pp. 112-115.
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Nguyen T. N., May J. A. Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes // Organic Letters. 2017. Vol. 20. No. 1. pp. 112-115.
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TY - JOUR
DO - 10.1021/acs.orglett.7b03349
UR - https://doi.org/10.1021/acs.orglett.7b03349
TI - Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes
T2 - Organic Letters
AU - Nguyen, Truong N
AU - May, Jeremy A.
PY - 2017
DA - 2017/12/14
PB - American Chemical Society (ACS)
SP - 112-115
IS - 1
VL - 20
PMID - 29239616
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2017_Nguyen,
author = {Truong N Nguyen and Jeremy A. May},
title = {Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes},
journal = {Organic Letters},
year = {2017},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.orglett.7b03349},
number = {1},
pages = {112--115},
doi = {10.1021/acs.orglett.7b03349}
}
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Nguyen, Truong N., and Jeremy A. May. “Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes.” Organic Letters, vol. 20, no. 1, Dec. 2017, pp. 112-115. https://doi.org/10.1021/acs.orglett.7b03349.