Homoallylically controlled epoxidation of Δ4-cis-1,2-disubstituted cyclohexenes

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18 Citations (Scopus)

Abstract

Stereochemical control during the epoxidation of cis-1-[N-Cbz]-2-[hydroxymethyl]-cyclohex-4-enes with MCPBA is dependent on hydroxyl functionalization which apparently determines ring conformation. Unprotected or acetate-derivatized compounds afford exclusively syn epoxide products. Silyl ether protected analogs furnish predominantly products derived from anti delivery of oxygen. Respective 2-carbomethoxy and benzyl carbamate-protected aminomethyl derivatives show stereospecificity similar to the free hydroxyl and acetate-protected substrates.

Original languageEnglish
Pages (from-to)1913-1916
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number15
DOIs
StatePublished - 1 Jan 1989

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Cyclohexenes
Epoxidation
Hydroxyl Radical
Acetates
Carbamates
Epoxy Compounds
Ether
Conformations
Oxygen
Derivatives
Substrates

Cite this

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title = "Homoallylically controlled epoxidation of Δ4-cis-1,2-disubstituted cyclohexenes",
abstract = "Stereochemical control during the epoxidation of cis-1-[N-Cbz]-2-[hydroxymethyl]-cyclohex-4-enes with MCPBA is dependent on hydroxyl functionalization which apparently determines ring conformation. Unprotected or acetate-derivatized compounds afford exclusively syn epoxide products. Silyl ether protected analogs furnish predominantly products derived from anti delivery of oxygen. Respective 2-carbomethoxy and benzyl carbamate-protected aminomethyl derivatives show stereospecificity similar to the free hydroxyl and acetate-protected substrates.",
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Homoallylically controlled epoxidation of Δ4-cis-1,2-disubstituted cyclohexenes. / Rotella, David.

In: Tetrahedron Letters, Vol. 30, No. 15, 01.01.1989, p. 1913-1916.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Homoallylically controlled epoxidation of Δ4-cis-1,2-disubstituted cyclohexenes

AU - Rotella, David

PY - 1989/1/1

Y1 - 1989/1/1

N2 - Stereochemical control during the epoxidation of cis-1-[N-Cbz]-2-[hydroxymethyl]-cyclohex-4-enes with MCPBA is dependent on hydroxyl functionalization which apparently determines ring conformation. Unprotected or acetate-derivatized compounds afford exclusively syn epoxide products. Silyl ether protected analogs furnish predominantly products derived from anti delivery of oxygen. Respective 2-carbomethoxy and benzyl carbamate-protected aminomethyl derivatives show stereospecificity similar to the free hydroxyl and acetate-protected substrates.

AB - Stereochemical control during the epoxidation of cis-1-[N-Cbz]-2-[hydroxymethyl]-cyclohex-4-enes with MCPBA is dependent on hydroxyl functionalization which apparently determines ring conformation. Unprotected or acetate-derivatized compounds afford exclusively syn epoxide products. Silyl ether protected analogs furnish predominantly products derived from anti delivery of oxygen. Respective 2-carbomethoxy and benzyl carbamate-protected aminomethyl derivatives show stereospecificity similar to the free hydroxyl and acetate-protected substrates.

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