C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines
Publication type: Journal Article
Publication date: 2013-01-29
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
23356473
Organic Chemistry
Abstract
The synthesis and alkylation of chiral, nonracemic tropane- and homotropane-derived enamines is examined as an approach to enantioenriched α-alkylated aldehydes. The two bicyclic N auxiliaries, which differ by a single methylene group, give opposite senses of asymmetric induction on alkylation with EtI and provide modestly enantioenriched 2-ethylhexanal (following hydrolysis of the alkylated iminium). The observed stereoselectivity is supported by density functional studies of ethylation for both enamines.
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14
Total citations:
14
Citations from 2024:
1
(7.14%)
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GOST
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Hodgson D. M. et al. C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines // Journal of Organic Chemistry. 2013. Vol. 78. No. 4. pp. 1508-1518.
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Hodgson D. M., Charlton A., Paton R. F., Thompson A. C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines // Journal of Organic Chemistry. 2013. Vol. 78. No. 4. pp. 1508-1518.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo3025972
UR - https://doi.org/10.1021/jo3025972
TI - C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines
T2 - Journal of Organic Chemistry
AU - Hodgson, David M.
AU - Charlton, Andrew
AU - Paton, Robert F.
AU - Thompson, Amber
PY - 2013
DA - 2013/01/29
PB - American Chemical Society (ACS)
SP - 1508-1518
IS - 4
VL - 78
PMID - 23356473
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2013_Hodgson,
author = {David M. Hodgson and Andrew Charlton and Robert F. Paton and Amber Thompson},
title = {C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines},
journal = {Journal of Organic Chemistry},
year = {2013},
volume = {78},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/jo3025972},
number = {4},
pages = {1508--1518},
doi = {10.1021/jo3025972}
}
Cite this
MLA
Copy
Hodgson, David M., et al. “C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines.” Journal of Organic Chemistry, vol. 78, no. 4, Jan. 2013, pp. 1508-1518. https://doi.org/10.1021/jo3025972.