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

David P. Rotella

doi:10.1016/S0040-4039(00)99612-6

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

David P. Rotella

Chemistry and Biochemistry

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17 Scopus citations

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 language	English
Pages (from-to)	1913-1916
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(00)99612-6
State	Published - 1989

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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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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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U2 - 10.1016/S0040-4039(00)99612-6

DO - 10.1016/S0040-4039(00)99612-6

M3 - Article

AN - SCOPUS:0000696953

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

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

Abstract

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