Asymmetric desymmetrization: Simultaneous stereocontrol of multichiral centers

被引：21

作者：

Mikami, K ^{[1
]}

Yoshida, A ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Meguro Ku, Tokyo 1528552, Japan

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2002年 / 60卷 / 08期

关键词：

asymmetric synthesis; asymmetric desymmetrization; enantiotopic group; meso compound; ene reaction; binaphthol; titanium;

D O I：

10.5059/yukigoseikyokaishi.60.732

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric desymmetrization is an efficient and powerful methodology for optically active substances with complex structures. Enantiotopic group differentiation reactions starting from meso compound with chiral centers can afford chiral/non-racemic compounds bearing controlled multi-chiral centers. We introduce many useful examples of asymmetric desymmetrization, which have ever been reported, and our results on asymmetric desymmetrization using asymmetric ene reactions catalyzed by chiral BINOL-Ti complex.

引用

页码：732 / 739

页数：8

共 61 条

[1] IS THE MECHANISM OF THE PROLINE-CATALYZED ENANTIOSELECTIVE ALDOL REACTION RELATED TO BIOCHEMICAL PROCESSES [J].

AGAMI, C ;

PUCHOT, C ;

SEVESTRE, H .

TETRAHEDRON LETTERS, 1986, 27 (13) :1501-1504

[2] A NEW DIAGNOSTIC-TOOL FOR ELUCIDATING THE MECHANISM OF ENANTIOSELECTIVE REACTIONS - APPLICATION TO THE HAJOS-PARRISH REACTION [J].

AGAMI, C ;

LEVISALLES, J ;

PUCHOT, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (08) :441-442

[3]

[Anonymous], 1971, SYMMETRIC ORGANIC RE

[4] CHIRAL CYCLOPENTANOID SYNTHETIC INTERMEDIATES VIA ASYMMETRIC MICROBIAL REDUCTION OF PROCHIRAL 2,2-DISUBSTITUTED CYCLOPENTANEDIONES [J].

BROOKS, DW ;

GROTHAUS, PG ;

IRWIN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) :2820-2821

[5] A HIGHLY ENANTIOSELECTIVE HYDROLYSIS OF CIS-3,5-DIACETOXYCYCLOPENT-1-ENE - AN ENZYMATIC PREPARATION OF 3(R)-ACETOXY-5(S)-HYDROXYCYCLOPENT-1-ENE [J].

DEARDORFF, DR ;

MATTHEWS, AJ ;

MCMEEKIN, DS ;

CRANEY, CL .

TETRAHEDRON LETTERS, 1986, 27 (11) :1255-1256

[6] DIASTEREOCONTROL FOR HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS OF CYCLOALKYL DIAZOACETATES [J].

DOYLE, MP ;

DYATKIN, AB ;

ROOS, GHP ;

CANAS, F ;

PIERSON, DA ;

VANBASTEN, A ;

MULLER, P ;

POLLEUX, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4507-4508

[7] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

[8] ENANTIOSELECTIVE LACTONIZATION OF SODIUM 4-HYDROXYPIMELATE UNDER ABIOLOGICAL CONDITIONS [J].

FUJI, K ;

NODE, M ;

TERADA, S ;

MURATA, M ;

NAGASAWA, H ;

TAGA, T ;

MACHIDA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (22) :6404-6406

[9] SYNTHESIS OF OPTICALLY-ACTIVE 3-OXA-CARBACYCLIN PRECURSORS FEATURING ASYMMETRIC HORNER-EMMONS REACTION [J].

GAIS, HJ ;

SCHMIEDL, G ;

BALL, WA ;

BUND, J ;

HELLMANN, G ;

ERDELMEIER, I .

TETRAHEDRON LETTERS, 1988, 29 (15) :1773-1774

[10]

Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2923, DOI 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO

← 1 2 3 4 5 6 7 →