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

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

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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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.",

author = "Rotella, \{David P.\}",

year = "1989",

doi = "10.1016/S0040-4039(00)99612-6",

language = "English",

volume = "30",

pages = "1913--1916",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "15",

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

AU - Rotella, David P.

PY - 1989

Y1 - 1989

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.

UR - https://www.scopus.com/pages/publications/0000696953

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

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

M3 - Article

AN - SCOPUS:0000696953

SN - 0040-4039

VL - 30

SP - 1913

EP - 1916

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

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

Abstract

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