Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane

John M. Gardiner; Marck Nørret; Ian H. Sadler

doi:10.1016/0040-4039(96)01915-6

Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane

John M. Gardiner, Marck Nørret, Ian H. Sadler

Research output: Contribution to journal › Article

3 Citations (Scopus)

Abstract

Epoxidation using a (salen)Mn catalyst shows complete selectivity between 2,6-trans and 2,6-cis dimethylbenzylidene cyclohexanes, is diastereospecific, and exhibits a kinetic resolution with k(rel)=5. Stereochemistry and conformation of the product 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane were determined by DQF-COSY and nOe difference measurements at 600MHz.

Original language	English
Pages (from-to)	8447-8450
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	46
DOIs	https://doi.org/10.1016/0040-4039(96)01915-6
Publication status	Published - 11 Nov 1996
Externally published	Yes

Access to Document

10.1016/0040-4039(96)01915-6

Link to publication in Scopus

Fingerprint Dive into the research topics of 'Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane'. Together they form a unique fingerprint.

Cite this

@article{6a8e2aaf1f1a46cd8b96bc85d5dac5a2,

title = "Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane",

abstract = "Epoxidation using a (salen)Mn catalyst shows complete selectivity between 2,6-trans and 2,6-cis dimethylbenzylidene cyclohexanes, is diastereospecific, and exhibits a kinetic resolution with k(rel)=5. Stereochemistry and conformation of the product 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane were determined by DQF-COSY and nOe difference measurements at 600MHz.",

author = "Gardiner, {John M.} and Marck N{\o}rret and Sadler, {Ian H.}",

year = "1996",

month = nov,

day = "11",

doi = "10.1016/0040-4039(96)01915-6",

language = "English",

volume = "37",

pages = "8447--8450",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Pergamon",

number = "46",

}

TY - JOUR

T1 - Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane

AU - Gardiner, John M.

AU - Nørret, Marck

AU - Sadler, Ian H.

PY - 1996/11/11

Y1 - 1996/11/11

N2 - Epoxidation using a (salen)Mn catalyst shows complete selectivity between 2,6-trans and 2,6-cis dimethylbenzylidene cyclohexanes, is diastereospecific, and exhibits a kinetic resolution with k(rel)=5. Stereochemistry and conformation of the product 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane were determined by DQF-COSY and nOe difference measurements at 600MHz.

AB - Epoxidation using a (salen)Mn catalyst shows complete selectivity between 2,6-trans and 2,6-cis dimethylbenzylidene cyclohexanes, is diastereospecific, and exhibits a kinetic resolution with k(rel)=5. Stereochemistry and conformation of the product 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane were determined by DQF-COSY and nOe difference measurements at 600MHz.

UR - http://www.scopus.com/inward/record.url?scp=16044375009&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(96)01915-6

DO - 10.1016/0040-4039(96)01915-6

M3 - Article

AN - SCOPUS:16044375009

VL - 37

SP - 8447

EP - 8450

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -