Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization
1
Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan
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Publication type: Journal Article
Publication date: 1993-03-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The α-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I 2 and s-collidine. The chiral iodides 2 thus obtained were converted to the α-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.
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KITAGAWA O. et al. Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization // Tetrahedron Letters. 1993. Vol. 34. No. 13. pp. 2165-2168.
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KITAGAWA O., Hanano T., Kikuchi N., TAGUCHI T. Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization // Tetrahedron Letters. 1993. Vol. 34. No. 13. pp. 2165-2168.
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TY - JOUR
DO - 10.1016/s0040-4039(00)60372-6
UR - https://doi.org/10.1016/s0040-4039(00)60372-6
TI - Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization
T2 - Tetrahedron Letters
AU - KITAGAWA, Osamu
AU - Hanano, Tokushi
AU - Kikuchi, Norihiko
AU - TAGUCHI, TAKEO
PY - 1993
DA - 1993/03/01
PB - Elsevier
SP - 2165-2168
IS - 13
VL - 34
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{1993_KITAGAWA,
author = {Osamu KITAGAWA and Tokushi Hanano and Norihiko Kikuchi and TAKEO TAGUCHI},
title = {Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization},
journal = {Tetrahedron Letters},
year = {1993},
volume = {34},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/s0040-4039(00)60372-6},
number = {13},
pages = {2165--2168},
doi = {10.1016/s0040-4039(00)60372-6}
}
Cite this
MLA
Copy
KITAGAWA, Osamu, et al. “Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization.” Tetrahedron Letters, vol. 34, no. 13, Mar. 1993, pp. 2165-2168. https://doi.org/10.1016/s0040-4039(00)60372-6.