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

Osamu Kitagawa; Tokushi Hanano; Norihiko Kikuchi; Takeo Taguchi

doi:10.1016/S0040-4039(00)60372-6

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

Osamu Kitagawa, Tokushi Hanano, Norihiko Kikuchi, Takeo Taguchi

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2165-2168
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(00)60372-6
Publication status	Published - 1993 Mar 26
Externally published	Yes

Keywords

asymmetric iodination
chiral pyrrolidine
iodolactonization
α-amino acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)60372-6

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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",

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day = "26",

doi = "10.1016/S0040-4039(00)60372-6",

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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

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

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

M3 - Article

AN - SCOPUS:0027409594

SN - 0040-4039

VL - 34

SP - 2165

EP - 2168

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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