Enantiocomplementary Preparation of ( S)- and ( R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount

被引：16

作者：

Bouzemi, Nassima ^{[1
]}

Grib, Ismahane ^{[1
]}

Houiene, Zahia ^{[1
]}

Aribi-Zouioueche, Louisa ^{[1
]}

机构：

[1] Badji Mokhtar Annaba Univ, Dept Chem, Ecocompatible Asymmetr Catalysis Lab LCAE, Annaba 23000, Algeria

来源：

CATALYSTS | 2014年 / 4卷 / 03期

关键词：

deracemisation; lipase; hydrolysis; stereoinversion; arylalkylcarbinol; DYNAMIC KINETIC RESOLUTION; SECONDARY ALCOHOLS; DERACEMIZATION; ACYLATION; ACID; BIOCATALYSIS; LIMITATIONS; ESTERS;

D O I：

10.3390/catal4030215

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%-99% ee and 76%-89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%-99% ee and 76%-89% yield.

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页码：215 / 225

页数：11

相关论文

共 37 条

[1] The FEMA GRAS assessment of aromatic substituted secondary alcohols, ketones, and related esters used as flavor ingredients [J].

Adams, T. B. ;

McGowen, M. M. ;

Williams, M. C. ;

Cohen, S. M. ;

Feron, V. J. ;

Goodman, J. I. ;

Marnett, L. J. ;

Munro, I. C. ;

Portoghese, P. S. ;

Smith, R. L. ;

Waddell, W. J. .

FOOD AND CHEMICAL TOXICOLOGY, 2007, 45 (02) :171-201

[2] Applications of enzymatic and non-enzymatic methods to access enantiomerically pure compounds using kinetic resolution and racemisation [J].

Ahmed, Marwa ;

Kelly, Tamsin ;

Ghanem, Ashraf .

TETRAHEDRON, 2012, 68 (34) :6781-6802

[3] Kinetic resolution of 1-acenaphthenol and 1-acetoxynaphthene through lipase-catalyzed acylation and hydrolysis [J].

Aribi-Zouioueche, L ;

Fiaud, JC .

TETRAHEDRON LETTERS, 2000, 41 (21) :4085-4088

[4] Effect of reaction parameters on synthesis of citronellyl methacrylate by lipase-catalyzed transesterification [J].

Athawale, V ;

Manjrekar, N ;

Athawale, M .

BIOTECHNOLOGY PROGRESS, 2003, 19 (02) :298-302

[5] Combined lipase-catalyzed resolution/Mitsunobu esterification for the production of enantiomerically enriched arylalkyl carbinols [J].

Bouzemi, N ;

Aribi-Zouioueche, L ;

Fiaud, JC .

TETRAHEDRON-ASYMMETRY, 2006, 17 (05) :797-800

[6] On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalyzed acylation [J].

Bouzemi, N ;

Debbeche, H ;

Aribi-Zouioueche, L ;

Fiaud, JC .

TETRAHEDRON LETTERS, 2004, 45 (03) :627-630

[7] Enzymatic resolution of 1,1-dimethoxybut-3-en-2-ol and 1,1-dimethoxypent-4-en-2-ol, α-hydroxyaldehyde precursors for aldol-type reactions [J].

Chênevert, R ;

Gravil, S ;

Bolte, J .

TETRAHEDRON-ASYMMETRY, 2005, 16 (12) :2081-2086

[8] PREPARATION OF (4S)-4-HYDROXY-3-METHYL-2-(2'-PROPYNYL)-2-CYCLOPENTENONE BY COMBINATION OF ENZYMATIC-HYDROLYSIS AND CHEMICAL TRANSFORMATION [J].

DANDA, H ;

MAEHARA, A ;

UMEMURA, T .

TETRAHEDRON LETTERS, 1991, 32 (38) :5119-5122

[9]

ERWIN GJC, 1993, TETRAHEDRON, V49, P1063

[10] Acetylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B: An experimental and computational study [J].

Escorcia, Andres M. ;

Molina, Daniel ;

Daza, Martha C. ;

Doerr, Markus .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 98 :21-29

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