Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate
Publication type: Journal Article
Publication date: 2005-05-27
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
15989321
Organic Chemistry
Abstract
N-Sulfinyl δ-amino β-ketoester enaminones, a new sulfinimine-derived chiral building block, undergoes, on hydrolysis in one pot, an intramolecular Michael addition followed by a retro-Michael-type elimination to give enantiopure 2,4,5-trisubstituted piperidines, a structural motif found in numerous biologically active alkaloids. This new chiral building block is readily prepared by treating N-sulfinyl δ-amino β-ketoesters with dimethylformamide dimethyl acetal. This new protocol was illustrated with a concise formal asymmetric synthesis of marine alkaloid pseudodistomin B triacetate.
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Total citations:
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Citations from 2024:
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GOST
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Davis F. A. et al. Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate // Journal of Organic Chemistry. 2005. Vol. 70. No. 14. pp. 5413-5419.
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Davis F. A., Zhang J., Li Y., He X., DeBrosse C. Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate // Journal of Organic Chemistry. 2005. Vol. 70. No. 14. pp. 5413-5419.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo050373o
UR - https://doi.org/10.1021/jo050373o
TI - Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate
T2 - Journal of Organic Chemistry
AU - Davis, Franklin A.
AU - Zhang, Junyi
AU - Li, Yingxin
AU - He, Xu
AU - DeBrosse, Charles
PY - 2005
DA - 2005/05/27
PB - American Chemical Society (ACS)
SP - 5413-5419
IS - 14
VL - 70
PMID - 15989321
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Davis,
author = {Franklin A. Davis and Junyi Zhang and Yingxin Li and Xu He and Charles DeBrosse},
title = {Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate},
journal = {Journal of Organic Chemistry},
year = {2005},
volume = {70},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo050373o},
number = {14},
pages = {5413--5419},
doi = {10.1021/jo050373o}
}
Cite this
MLA
Copy
Davis, Franklin A., et al. “Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B Triacetate.” Journal of Organic Chemistry, vol. 70, no. 14, May. 2005, pp. 5413-5419. https://doi.org/10.1021/jo050373o.