ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE, CATALYZED BY (S)-(-)-PROLINE OR (S)-(+)-PROLINOL

被引：67

作者：

BRUNEL, JM ^{[1
]}

MAFFEI, M ^{[1
]}

BUONO, G ^{[1
]}

机构：

[1] UNIV AIX MARSEILLE 3,ENSSPICAM,URA REACT CATALYSE 1410,AVE ESCADRILLE NORMANDIE NIEMEN,F-13397 MARSEILLE 13,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(00)80075-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective reduction of ketones by borane in the presence of catalytic amounts of (S)-(-)-proline or (S)-(+)-prolinol as chiral auxiliaries has been investigated. The alcohols possess all the (R) configuration, and are obtained in good enantiomeric excess. A mechanistic rationale is proposed, involving an oxazaborolidine formed from (S)-(+)-prolinol and borane.

引用

页码：2255 / 2260

页数：6

共 22 条

[1] THE USE OF (4R,5R)-DICARBOALKOXY-2-CHLORO-1,3,2-DIOXAPHOSPHOLANES AS NEW CHIRAL DERIVATIZING AGENTS FOR THE DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS BY P-31 NMR [J].

BRUNEL, JM ;

PARDIGON, O ;

MAFFEI, M ;

BUONO, G .

TETRAHEDRON-ASYMMETRY, 1992, 3 (10) :1243-1246

[2]

CHO BT, 1992, TETRAHEDRON-ASYMMETR, V3, P73

[3] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[4] X-RAY CRYSTAL-STRUCTURE OF A CHIRAL OXAZABOROLIDINE CATALYST FOR ENANTIOSELECTIVE CARBONYL REDUCTION [J].

COREY, EJ ;

AZIMIOARA, M ;

SARSHAR, S .

TETRAHEDRON LETTERS, 1992, 33 (24) :3429-3430

[5] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[6] ASYMMETRIC REDUCTION OF ALIPHATIC-KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE [J].

ITSUNO, S ;

ITO, K ;

HIRAO, A ;

NAKAHAMA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :555-557

[7] ASYMMETRIC-SYNTHESIS USING CHIRALLY MODIFIED BOROHYDRIDES .4. ENANTIO-SELECTIVE REDUCTION OF KETONES AND OXIME ETHERS WITH THE REAGENT PREPARED FROM BORANE AND POLYMER-SUPPORTED (S)-(-)-2-AMINO-3-(PARA-HYDROXYPHENYL)-1,1-DIPHENYLPROPAN-1-OL [J].

ITSUNO, S ;

NAKANO, M ;

ITO, K ;

HIRAO, A ;

OWA, M ;

KANDA, N ;

NAKAHAMA, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2615-2619

[8] ASYMMETRIC REDUCTION OF AROMATIC KETONE IN A CONTINUOUS-FLOW SYSTEM [J].

ITSUNO, S ;

ITO, K ;

MARUYAMA, T ;

KANDA, N ;

HIRAO, A ;

NAKAHAMA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (10) :3329-3331

[9] ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES - SYNTHESES AND APPLICATION OF 2 CHIRAL BETA-AMINO ALCOHOLS FROM (S)-2-INDOLINE CARBOXYLIC-ACID [J].

MARTENS, J ;

DAUELSBERG, C ;

BEHNEN, W ;

WALLBAUM, S .

TETRAHEDRON-ASYMMETRY, 1992, 3 (03) :347-350

[10] A PRACTICAL PROCESS FOR THE PREPARATION OF TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C]-[1,3,2]OXAZABOROLE BORANE - A HIGHLY ENANTIOSELECTIVE STOICHIOMETRIC AND CATALYTIC REDUCING AGENT [J].

MATHRE, DJ ;

THOMPSON, AS ;

DOUGLAS, AW ;

HOOGSTEEN, K ;

CARROLL, JD ;

CORLEY, EG ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2880-2888

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