ENANTIOSELECTIVE PROTONATION OF SAMARIUM ENOLATES BY A C-2-SYMMETRICAL CHIRAL DIOL

被引：36

作者：

TAKEUCHI, S

OHIRA, A

MIYOSHI, N

MASHIO, H

OHGO, Y

机构：

[1] Niigata College of Pharmacy, Niigata, 950-21

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 09期

关键词：

D O I：

10.1016/0957-4166(94)80086-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.

引用

收藏

页码：1763 / 1780

页数：18

相关论文

共 45 条

[1] STEREOSPECIFIC FORMATION OF ENOLATES FROM REACTION OF UNSYMMETRICAL KETENES AND ORGANO-LITHIUM REAGENTS [J].

BAIGRIE, LM ;

SEIKLAY, HR ;

TIDWELL, TT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5391-5396

[2] SAMARIUM DIIODIDE MEDIATED REDUCTION OF ALLYL HALIDES - A NEW REDUCTIVE APPROACH TO EXOMETHYLENE CEPHAMS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A .

TETRAHEDRON LETTERS, 1993, 34 (43) :6931-6934

[3] THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].

CURRAN, DP ;

TOTLEBEN, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058

[4]

CURRAN DP, 1992, SYNLETT, P943

[5]

DEHMLOW EV, 1979, LIEBIGS ANN CHEM, P572

[6] ENANTIOSELECTIVITY IN ENEDIOL-HYDROXYKETONE TAUTOMERIZATION [J].

DUHAMEL, L ;

LAUNAY, JC .

TETRAHEDRON LETTERS, 1983, 24 (39) :4209-4212

[7] A CHIRAL SAMARIUM-BASED CATALYST FOR THE ASYMMETRIC MEERWEIN-PONNDORF-VERLEY REDUCTION [J].

EVANS, DA ;

NELSON, SG ;

GAGNE, MR ;

MUCI, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9800-9801

[8] HIGHLY ENANTIOSELECTIVE PROTONATION OF THIOL ESTER ENOLATES [J].

FEHR, C ;

STEMPF, I ;

GALINDO, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1042-1044

[9] SYNTHESIS OF (R)-(+)-ALPHA-DAMASCONE AND (S)-(-)-ALPHA-DAMASCONE BY TANDEM GRIGNARD REACTION-ENANTIOSELECTIVE PROTONATION - EVIDENCE FOR THE INTERMEDIACY OF A CHIRAL COMPLEX [J].

FEHR, C ;

GALINDO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6909-6911

[10] ENANTIOSELECTIVE ADDITION OF AROMATIC THIOLS TO A KETENE [J].

FEHR, C ;

STEMPF, I ;

GALINDO, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1044-1046

← 1 2 3 4 5 →