Asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton

被引：24

作者：

Kanda, Y ^{[1
]}

Onomura, O ^{[1
]}

Maki, T ^{[1
]}

Matsumura, Y ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Dept Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

CHIRALITY | 2003年 / 15卷 / 01期

关键词：

catalytic asymmetric synthesis; carbon-carbon formation; optically active 2-piperidylacetate; copper ion-catalyzed; dimethyl malonate; bisoxazoline;

D O I：

10.1002/chir.10151

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton was exploited. This method consisted of a reaction between 1-(4-methoxybenzoyl)-3,4-didehydro-2-methoxypiperidines and dimethyl malonate catalyzed by Cu(II)-chiral 2,2'-isopropylidenebis(4-phenyl-2-oxazoline) to afford a 2-substituted piperidine skeleton with moderate enantioselectivity. (C) 2002 Wiley-Liss, Inc.

引用

页码：89 / 94

页数：6

共 14 条

[1] Asymmetric routes to substituted piperidines [J].

Bailey, PD ;

Millwood, PA ;

Smith, PD .

CHEMICAL COMMUNICATIONS, 1998, (06) :633-640

[2] Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions [J].

Johnson, JS ;

Evans, DA .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :325-335

[3]

Laschat S, 2000, SYNTHESIS-STUTTGART, P1781

[4] A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine [J].

Matsumura, Y ;

Kanda, Y ;

Shirai, K ;

Onomura, O ;

Maki, T .

ORGANIC LETTERS, 1999, 1 (02) :175-178

[5] A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction [J].

Matsumura, Y ;

Kanda, Y ;

Shirai, K ;

Onomura, O ;

Maki, T .

TETRAHEDRON, 2000, 56 (38) :7411-7422

[6] Copper ion-catalyzed asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton [J].

Onomura, O ;

Kanda, Y ;

Nakamura, Y ;

Maki, T ;

Matsumura, Y .

TETRAHEDRON LETTERS, 2002, 43 (17) :3229-3231

[7]

Plunkett O, 1998, RODDS CHEM, V4, P365

[8] ELECTROORGANIC CHEMISTRY .46. A NEW CARBON-CARBON BOND FORMING REACTION AT THE ALPHA-POSITION OF AMINES UTILIZING ANODIC-OXIDATION AS A KEY STEP [J].

SHONO, T ;

MATSUMURA, Y ;

TSUBATA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1172-1176

[9] ELECTROORGANIC CHEM .96. SYNTHESIS OF OPTICALLY-ACTIVE PIPERIDINE AND PYRROLIDINE ALKALOIDS FROM L-LYSINE, L-ORNITHINE, OR L-PROLINE USING ANODIC-OXIDATION AS KEY STEPS [J].

SHONO, T ;

MATSUMURA, Y ;

TSUBATA, K ;

UCHIDA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13) :2590-2592

[10] ELECTROORGANIC CHEM .109. A NEW METHOD FOR INTRODUCING SOME ACTIVE METHYLENE OR METHINE GROUPS TO THE 3-POSITION OF PYRROLIDINE OR PIPERIDINE SKELETON, AND ITS APPLICATION TO PREPARATION OF A KEY INTERMEDIATE FOR (+/-)-EBURNAMONINE SYNTHESIS [J].

SHONO, T ;

MATSUMURA, Y ;

OGAKI, M ;

ONOMURA, O .

CHEMISTRY LETTERS, 1987, (07) :1447-1450

← 1 2 →