Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters

Miguel Díaz; Vicenç Branchadell; Antoni Oliva; Rosa M. Ortuño

doi:10.1016/0040-4020(95)00745-T

Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters

Miguel Díaz, Vicenç Branchadell, Antoni Oliva, Rosa M. Ortuño

Department of Chemistry

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

13 Citations (Scopus)

Abstract

Enantiomeric epoxides have been synthetized in efficient and diastereoselective manner through the respective cycloadditions of diazomethane to the carbonyl group of antipodal cyclopentyl ketones. These epoxy derivatives are potent synthetic building blocks which have been used as versatile precursors to several enantiopure title compounds, these being molecules with a high functional density that bear, at least, four stereogenic centers in the cyclopentane ring and a quaternary stereocenter in the side-chain. © 1995 Elsevier Science Ltd Printed in Great Britain. All rights reserved.

Original language	English
Pages (from-to)	11841-11854
Journal	Tetrahedron
Volume	51
Issue number	43
DOIs	https://doi.org/10.1016/0040-4020(95)00745-T
Publication status	Published - 23 Oct 1995

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title = "Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters",

abstract = "Enantiomeric epoxides have been synthetized in efficient and diastereoselective manner through the respective cycloadditions of diazomethane to the carbonyl group of antipodal cyclopentyl ketones. These epoxy derivatives are potent synthetic building blocks which have been used as versatile precursors to several enantiopure title compounds, these being molecules with a high functional density that bear, at least, four stereogenic centers in the cyclopentane ring and a quaternary stereocenter in the side-chain. {\textcopyright} 1995 Elsevier Science Ltd Printed in Great Britain. All rights reserved.",

author = "Miguel D{\'i}az and Vicen{\c c} Branchadell and Antoni Oliva and Ortu{\~n}o, {Rosa M.}",

year = "1995",

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T1 - Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters

AU - Díaz, Miguel

AU - Branchadell, Vicenç

AU - Oliva, Antoni

AU - Ortuño, Rosa M.

PY - 1995/10/23

Y1 - 1995/10/23

N2 - Enantiomeric epoxides have been synthetized in efficient and diastereoselective manner through the respective cycloadditions of diazomethane to the carbonyl group of antipodal cyclopentyl ketones. These epoxy derivatives are potent synthetic building blocks which have been used as versatile precursors to several enantiopure title compounds, these being molecules with a high functional density that bear, at least, four stereogenic centers in the cyclopentane ring and a quaternary stereocenter in the side-chain. © 1995 Elsevier Science Ltd Printed in Great Britain. All rights reserved.

AB - Enantiomeric epoxides have been synthetized in efficient and diastereoselective manner through the respective cycloadditions of diazomethane to the carbonyl group of antipodal cyclopentyl ketones. These epoxy derivatives are potent synthetic building blocks which have been used as versatile precursors to several enantiopure title compounds, these being molecules with a high functional density that bear, at least, four stereogenic centers in the cyclopentane ring and a quaternary stereocenter in the side-chain. © 1995 Elsevier Science Ltd Printed in Great Britain. All rights reserved.

U2 - 10.1016/0040-4020(95)00745-T

DO - 10.1016/0040-4020(95)00745-T

M3 - Article

VL - 51

SP - 11841

EP - 11854

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 43

ER -

Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters

Abstract

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