American Chemical Society (ACS)
Organic Letters
,  volume 21 ,  issue 13 ,  pages 5143-5146

Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones

Publication type: Journal Article
Publication date: 2019-06-20
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A novel phosphine-catalyzed intermolecular cyclization between 2-sulfonamidobenzaldehyes and ynones is reported. This methodology serves as a conduit for the construction of benzo[ b]azepin-3-ones in good to excellent yields under mild conditions. The resulting 2-benzylidene moieties are formed exclusively in the E-configuration. Mechanistically, this unusual annulation occurs through a phosphine-catalyzed α-umpolung addition, followed by an aldol reaction. One of the benzo[ b]azepin-3-one products was converted to the core structure of 3-amino-[ a]benzazepin-2-one-1-alkanoic acids, many of which function as angiotensin-converting enzyme inhibitors.
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GOST |
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GOST Copy
Zhang K. et al. Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones // Organic Letters. 2019. Vol. 21. No. 13. pp. 5143-5146.
GOST all authors (up to 50) Copy
Zhang K., Cai L., Hong S., Kwon O. Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones // Organic Letters. 2019. Vol. 21. No. 13. pp. 5143-5146.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.9b01749
UR - https://doi.org/10.1021/acs.orglett.9b01749
TI - Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones
T2 - Organic Letters
AU - Zhang, K.Z.
AU - Cai, Lingchao
AU - Hong, Sooji
AU - Kwon, Ohyun
PY - 2019
DA - 2019/06/20
PB - American Chemical Society (ACS)
SP - 5143-5146
IS - 13
VL - 21
PMID - 31247774
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Zhang,
author = {K.Z. Zhang and Lingchao Cai and Sooji Hong and Ohyun Kwon},
title = {Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.9b01749},
number = {13},
pages = {5143--5146},
doi = {10.1021/acs.orglett.9b01749}
}
MLA
Cite this
MLA Copy
Zhang, K.Z., et al. “Phosphine-Catalyzed α-Umpolung–Aldol Reaction for the Synthesis of Benzo[b]azapin-3-ones.” Organic Letters, vol. 21, no. 13, Jun. 2019, pp. 5143-5146. https://doi.org/10.1021/acs.orglett.9b01749.