Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

Osamu Kitagawa, Tokushi Hanano, Norihiko Kikuchi, Takeo Taguchi

研究成果: Article

39 引用 (Scopus)

抄録

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 I2 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.

元の言語English
ページ(範囲)2165-2168
ページ数4
ジャーナルTetrahedron Letters
34
発行部数13
DOI
出版物ステータスPublished - 1993 3 26
外部発表Yes

Fingerprint

Iodides
Lactones
Amides
Amino Acids
pyrrolidine
gamma-collidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization. / Kitagawa, Osamu; Hanano, Tokushi; Kikuchi, Norihiko; Taguchi, Takeo.

:: Tetrahedron Letters, 巻 34, 番号 13, 26.03.1993, p. 2165-2168.

研究成果: Article

@article{bd6f98eed98241e0bd290a940967337d,
title = "Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization",
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 I2 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.",
keywords = "asymmetric iodination, chiral pyrrolidine, iodolactonization, α-amino acid",
author = "Osamu Kitagawa and Tokushi Hanano and Norihiko Kikuchi and Takeo Taguchi",
year = "1993",
month = "3",
day = "26",
doi = "10.1016/S0040-4039(00)60372-6",
language = "English",
volume = "34",
pages = "2165--2168",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "13",

}

TY - JOUR

T1 - Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

AU - Kitagawa, Osamu

AU - Hanano, Tokushi

AU - Kikuchi, Norihiko

AU - Taguchi, Takeo

PY - 1993/3/26

Y1 - 1993/3/26

N2 - 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 I2 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.

AB - 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 I2 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.

KW - asymmetric iodination

KW - chiral pyrrolidine

KW - iodolactonization

KW - α-amino acid

UR - http://www.scopus.com/inward/record.url?scp=0027409594&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027409594&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)60372-6

DO - 10.1016/S0040-4039(00)60372-6

M3 - Article

AN - SCOPUS:0027409594

VL - 34

SP - 2165

EP - 2168

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 13

ER -