Tetrahedron Letters, volume 35, issue 35, pages 6427-6430

A mechanistically designed mono-cinchona alkaloid is an excellent catalyst for the enantioselective dihydroxylation of olefins

E J Corey ¹

Mark C. Noe ¹

Michael J Grogan ¹

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Department of Chemistry, Harvard University, Cambridge, Massachusetts, 02138 USA |

Publication type: Journal Article

Publication date: 1994-08-01

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)78237-2

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

On the basis of ideas recently advanced regarding the origin of enantioselectivity in the OsO 4 -promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1 , specifically strong evidence for reaction via transition state assembly 2 , the mono-quinidine derivative 3 was selected as a promising catalytic ligand. The experimental observation of high enantioselectivity promoted by 3 provides additional evidence in favor of transition-state 2 . Graphic

Found

	2 4 6 8 10
Tetrahedron Letters	Tetrahedron Letters, 10, 22.22% Tetrahedron Letters 10 publications, 22.22%
Journal of the American Chemical Society	Journal of the American Chemical Society, 3, 6.67% Journal of the American Chemical Society 3 publications, 6.67%
Organic Letters	Organic Letters, 3, 6.67% Organic Letters 3 publications, 6.67%
Tetrahedron Asymmetry	Tetrahedron Asymmetry, 3, 6.67% Tetrahedron Asymmetry 3 publications, 6.67%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 2.22% Journal of Organic Chemistry 1 publication, 2.22%
Tetrahedron	Tetrahedron, 1, 2.22% Tetrahedron 1 publication, 2.22%
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 1, 2.22% European Journal of Medicinal Chemistry 1 publication, 2.22%
Journal of Organometallic Chemistry	Journal of Organometallic Chemistry, 1, 2.22% Journal of Organometallic Chemistry 1 publication, 2.22%
Angewandte Chemie	Angewandte Chemie, 1, 2.22% Angewandte Chemie 1 publication, 2.22%
Journal of Heterocyclic Chemistry	Journal of Heterocyclic Chemistry, 1, 2.22% Journal of Heterocyclic Chemistry 1 publication, 2.22%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.22% European Journal of Organic Chemistry 1 publication, 2.22%
Chemical Reviews	Chemical Reviews, 1, 2.22% Chemical Reviews 1 publication, 2.22%
Advances in Physical Organic Chemistry	Advances in Physical Organic Chemistry, 1, 2.22% Advances in Physical Organic Chemistry 1 publication, 2.22%
Cumulative Index of Heterocyclic Systems	Cumulative Index of Heterocyclic Systems, 1, 2.22% Cumulative Index of Heterocyclic Systems 1 publication, 2.22%
Synthesis	Synthesis, 1, 2.22% Synthesis 1 publication, 2.22%
	2 4 6 8 10

	2 4 6 8 10 12 14 16 18
Elsevier	Elsevier, 17, 37.78% Elsevier 17 publications, 37.78%
American Chemical Society (ACS)	American Chemical Society (ACS), 8, 17.78% American Chemical Society (ACS) 8 publications, 17.78%
Wiley	Wiley, 5, 11.11% Wiley 5 publications, 11.11%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 2.22% Georg Thieme Verlag KG 1 publication, 2.22%
	2 4 6 8 10 12 14 16 18

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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)

A mechanistically designed mono-cinchona alkaloid is an excellent catalyst for the enantioselective dihydroxylation of olefins

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