Tetrahedron Letters, volume 33, issue 48, pages 7357-7360

Asymmetric vicinal acylation of olefins: A new approach to enantiomerically pure γ-lactones.

C. GENICOT ¹

L. Ghosez ¹

Laboratoire de Chimie Organique de Synthèse Université Catholique de Louvain Place Louis Pasteur, 1, Louvain-la Neuve, B-1348, Belgium |

Publication type: Journal Article

Publication date: 1992-11-01

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)60187-9

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

Amide 3 derived from N-tosylsarcosine and (2R,5R)-dimethylpyrrolidine was converted into keteniminium salt 4 which readily cycloadded to olefins. Hydrolysis of the adducts yielded cyclobutanones which were regiospecifically oxidized to gamma-lactones 7. High enantioselectivities were observed with 1,2-cis-disubstitued olefins.

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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 vicinal acylation of olefins: A new approach to enantiomerically pure γ-lactones.

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