Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides:: versatile synthons for enantiopure β-hydroxy sulfoxides

被引：19

作者：

Singh, S ^{[1
]}

Kumar, S ^{[1
]}

Chimni, SS ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(01)00434-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2457 / 2462

页数：6

共 54 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2] SYNTHESIS, CONFIGURATIONAL ASSIGNMENT, AND CONFORMATIONAL-ANALYSIS OF BETA-HYDROXY SULFOXIDES, BIOISOSTERES OF OXISURAN METABOLITES, AND THEIR O-METHYL DERIVATIVES [J].

ALVAREZIBARRA, C ;

CUERVORODRIGUEZ, R ;

FERNANDEZMONREAL, MC ;

RUIZ, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7284-7291

[3]

ANDERSEN KK, 1962, TETRAHEDRON LETT, P93

[4]

ARSENIO G, 2001, TETRAHEDRON-ASYMMETR, V11, P3481

[5]

ARSENIO G, 1998, TETRAHEDRON LETT, V39, P3277

[6] General synthesis of chiral β-hydroxy sulfones via enantioselective ruthenium-catalyzed hydrogenation [J].

Bertus, P ;

Phansavath, P ;

Ratovelomanana-Vidal, V ;

Genêt, JP ;

Touati, AR ;

Homri, T ;

Ben Hassine, B .

TETRAHEDRON LETTERS, 1999, 40 (16) :3175-3178

[7] STEREOCHEMISTRY OF ORGANIC SULFUR-COMPOUNDS .12. CONFIGURATIONAL ASSIGNMENT OF 2-METHYLSULPHINYL-1-PHENYLETHANOL AND SOME O-DERIVATIVES [J].

BRUNET, E ;

GRACIARUANO, JL ;

HOYOS, MA ;

RODRIGUEZ, JH ;

PRADOS, P ;

ALCUDIA, F .

ORGANIC MAGNETIC RESONANCE, 1983, 21 (10) :643-648

[8] STEREOSELECTIVE HYDRIDE REDUCTIONS OF CHIRAL 2-P-TOLYLSULFINYLCYCLOALKANONES [J].

BUENO, AB ;

CARRENO, M ;

RUANO, JLG ;

PENA, B ;

RUBIO, A ;

HOYOS, MA .

TETRAHEDRON, 1994, 50 (31) :9355-9364

[9] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[10] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

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