Optimization by Response Surface Methodology (RSM) of the Kharasch-Sosnovsky Oxidation of Valencene

被引：15

作者：

Garcia-Cabeza, Ana Leticia ^{[1
]}

Ray, Lindsey P. ^{[1
]}

Marin-Barrios, Ruben ^{[1
]}

Ortega, Maria J. ^{[1
]}

Moreno-Dorado, F. Javier ^{[1
]}

Guerra, Francisco M. ^{[1
]}

Massanet, Guillermo M. ^{[1
]}

机构：

[1] Univ Cadiz, Fac Ciencias, Dept Quim Organ, Puerto Real 11510, Spain

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2015年 / 19卷 / 11期

关键词：

C-H BONDS; CATALYZED ALLYLIC OXIDATION; EXPERIMENTAL-DESIGN; THAPSIGARGIN; OLEFINS; INHIBITOR; STRATEGY; TOOL;

D O I：

10.1021/op5002462

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Response surface methodology (RSM) has been employed to model and optimize the Kharasch-Spsnovsky allylic oxidation of valencene. The detailed effects of the amounts of oxidant, substrate, copper catalyst, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and temperature have been studied. The,concentration of substrate and quantity of oxidant have been determined as the most significant variables. The interaction effects on the yield have been investigated using a three-level full-factorial design. The yield of benzoyloxyvalencene has been improved to 99%. Analysis of variance (ANOVA) has been used to evaluate the goodness of fit of the model.

引用

页码：1662 / 1666

页数：5

共 47 条

[1] Terminal Olefins to Chromans, Isochromans, and Pyrans via Allylic C-H Oxidation [J].

Ammann, Stephen E. ;

Rice, Grant T. ;

White, M. Christina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10834-10837

[2] Copper catalyzed allylic oxidation with peresters [J].

Andrus, MB ;

Lashley, JC .

TETRAHEDRON, 2002, 58 (05) :845-866

[3] Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate [J].

Andrus, MB ;

Zhou, ZN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8806-8807

[4] Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis [J].

Andrus, MB ;

Asgari, D .

TETRAHEDRON, 2000, 56 (32) :5775-5780

[5] Theoretical Insights into Enantioselective Catalysis: The Mechanism of the Kharasch-Sosnovsky Reaction [J].

Antonio Mayoral, Jose ;

Rodriguez-Rodriguez, Sergio ;

Salvatella, Luis .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9274-9285

[6] Experimental design .2. Optimization [J].

Araujo, PW ;

Brereton, RG .

TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1996, 15 (02) :63-70

[7] Experimental design .1. Screening [J].

Araujo, PW ;

Brereton, RG .

TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1996, 15 (01) :26-31

[8] Total synthesis of thapsigargin, a potent SERCA pump inhibitor [J].

Ball, Matthew ;

Andrews, Stephen P. ;

Wierschem, Frank ;

Cleator, Ed ;

Smith, Martin D. ;

Ley, Steven V. .

ORGANIC LETTERS, 2007, 9 (04) :663-666

[9]

Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a

[10] REFLECTIONS ON THE MODIFIED SIMPLEX .1. [J].

BETTERIDGE, D ;

WADE, AP ;

HOWARD, AG .

TALANTA, 1985, 32 (8B) :709-722

← 1 2 3 4 5 →