Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines
Publication type: Journal Article
Publication date: 2018-03-28
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
29589946
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis- ortho-functionalized arene.
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Citations from 2025:
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GOST
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Shikora J. M., Chemler S. Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines // Organic Letters. 2018. Vol. 20. No. 8. pp. 2133-2137.
GOST all authors (up to 50)
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Shikora J. M., Chemler S. Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines // Organic Letters. 2018. Vol. 20. No. 8. pp. 2133-2137.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.8b00282
UR - https://doi.org/10.1021/acs.orglett.8b00282
TI - Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines
T2 - Organic Letters
AU - Shikora, Jonathan M
AU - Chemler, Sherry
PY - 2018
DA - 2018/03/28
PB - American Chemical Society (ACS)
SP - 2133-2137
IS - 8
VL - 20
PMID - 29589946
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Shikora,
author = {Jonathan M Shikora and Sherry Chemler},
title = {Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines},
journal = {Organic Letters},
year = {2018},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.8b00282},
number = {8},
pages = {2133--2137},
doi = {10.1021/acs.orglett.8b00282}
}
Cite this
MLA
Copy
Shikora, Jonathan M., and Sherry Chemler. “Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel–Crafts Addition of Phenols to N-Sulfonyl Aldimines.” Organic Letters, vol. 20, no. 8, Mar. 2018, pp. 2133-2137. https://doi.org/10.1021/acs.orglett.8b00282.