ASYMMETRIC HYDROGENATION OF 3,5-DIOXOESTERS CATALYZED BY RU-BINAP COMPLEX - A SHORT STEP ASYMMETRIC-SYNTHESIS OF 6-SUBSTITUTED 5,6-DIHYDRO-2-PYRONES

被引：78

作者：

SHAO, LM ^{[1
]}

KAWANO, H ^{[1
]}

SABURI, M ^{[1
]}

UCHIDA, Y ^{[1
]}

机构：

[1] UNIV TOKYO,FAC ENGN,DEPT IND CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 10期

关键词：

3,5-DIOXOESTER; RU-BINAP CATALYST; ASYMMETRIC HYDROGENATION; ASYMMETRIC SYNTHESIS; LACTONE;

D O I：

10.1016/S0040-4020(01)86300-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80% e.e.). The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c. It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the beta-diketone mode. A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.

引用

页码：1997 / 2010

页数：14

共 28 条

[21] ASYMMETRIC HYDROGENATION OF UNSATURATED CARBONYL-COMPOUNDS CATALYZED BY BINAP RU(II) COMPLEXES - ENANTIOSELECTIVE SYNTHESIS OF GAMMA-BUTYROLACTONES AND CYCLOPENTANONES [J].

OHTA, T ;

MIYAKE, T ;

SEIDO, N ;

KUMOBAYASHI, H ;

AKUTAGAWA, S ;

TAKAYA, H .

TETRAHEDRON LETTERS, 1992, 33 (05) :635-638

[22] THE SYNTHESIS OF MEVINIC ACIDS [J].

ROSEN, T ;

HEATHCOCK, CH .

TETRAHEDRON, 1986, 42 (18) :4909-4951

[23] SYNTHESIS OF A CHIRAL SYNTHON FOR THE LACTONE PORTION OF COMPACTIN AND MEVINOLIN [J].

ROTH, BD ;

ROARK, WH .

TETRAHEDRON LETTERS, 1988, 29 (11) :1255-1258

[24] STEREOCHEMISTRY OF ALTERNATING POLYOL CHAINS - C-13 NMR ANALYSIS OF 1,3-DIOL ACETONIDES [J].

RYCHNOVSKY, SD ;

SKALITZKY, DJ .

TETRAHEDRON LETTERS, 1990, 31 (07) :945-948

[25]

SHAO L, 1991, TETRAHEDRON LETT, V52, P7699

[26] ENANTIOCONTROLLED AND STEREOCONTROLLED CONSTRUCTION OF TERTIARY AND QUATERNARY CARBON CENTERS USING CHIRAL O-BENZYLGLYCIDOL AS TEMPLATE [J].

TAKANO, S ;

SHIMAZAKI, Y ;

MORIYA, M ;

OGASAWARA, K .

CHEMISTRY LETTERS, 1990, (07) :1177-1180

[27]

TAKANO S, 1989, SYNTHESIS-STUTTGART, P539

[28] NEW CHIRAL RUTHENIUM COMPLEXES FOR ASYMMETRIC CATALYTIC HYDROGENATIONS [J].

TAKAYA, H ;

OHTA, T ;

MASHIMA, K ;

NOYORI, R .

PURE AND APPLIED CHEMISTRY, 1990, 62 (06) :1135-1138

← 1 2 3 →