Tetrahedron Letters, volume 34, issue 13, pages 2165-2168

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

Osamu KITAGAWA ¹

Tokushi Hanano ¹

Norihiko Kikuchi ¹

TAKEO TAGUCHI ¹

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Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan |

Publication type: Journal Article

Publication date: 1993-03-01

Elsevier

Journal: Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.323

CiteScore: 3.5

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/s0040-4039(00)60372-6

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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.

Found

	1 2 3 4 5 6
Tetrahedron	Tetrahedron, 6, 20% Tetrahedron 6 publications, 20%
Tetrahedron Letters	Tetrahedron Letters, 5, 16.67% Tetrahedron Letters 5 publications, 16.67%
Tetrahedron Asymmetry	Tetrahedron Asymmetry, 2, 6.67% Tetrahedron Asymmetry 2 publications, 6.67%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 2, 6.67% European Journal of Organic Chemistry 2 publications, 6.67%
Synthesis	Synthesis, 2, 6.67% Synthesis 2 publications, 6.67%
Organic Letters	Organic Letters, 1, 3.33% Organic Letters 1 publication, 3.33%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 3.33% Journal of the American Chemical Society 1 publication, 3.33%
Synthetic Communications	Synthetic Communications, 1, 3.33% Synthetic Communications 1 publication, 3.33%
Organic Preparations and Procedures International	Organic Preparations and Procedures International, 1, 3.33% Organic Preparations and Procedures International 1 publication, 3.33%
Advances in Carbohydrate Chemistry and Biochemistry	Advances in Carbohydrate Chemistry and Biochemistry, 1, 3.33% Advances in Carbohydrate Chemistry and Biochemistry 1 publication, 3.33%
	1 2 3 4 5 6

	2 4 6 8 10 12 14
Elsevier	Elsevier, 14, 46.67% Elsevier 14 publications, 46.67%
Wiley	Wiley, 6, 20% Wiley 6 publications, 20%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 6.67% American Chemical Society (ACS) 2 publications, 6.67%
Taylor & Francis	Taylor & Francis, 2, 6.67% Taylor & Francis 2 publications, 6.67%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 2, 6.67% Georg Thieme Verlag KG 2 publications, 6.67%
	2 4 6 8 10 12 14

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Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.323

CiteScore

3.5

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)

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

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