Oxazaborolidine-catalysed reduction of alk-2-ene-1,4diones.: A convenient access to chiral 1,4-diols

被引：35

作者：

Bach, J ^{[1
]}

Berenguer, R ^{[1
]}

Garcia, J ^{[1
]}

López, M ^{[1
]}

Manzanal, J ^{[1
]}

Vilarrasa, J ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Div 3, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

asymmetric synthesis; diols; oxazaborolidines; reduction;

D O I：

10.1016/S0040-4020(98)00936-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of C-2-symmetric, chiral alk-2-ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)-1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenriched compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14947 / 14962

页数：16

共 53 条

[1] Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols
Bach, J
Berenguer, R
Garcia, J
Loscertales, T
Manzanal, J
Vilarrasa, J
[J]. TETRAHEDRON LETTERS, 1997, 38 (06) : 1091 - 1094
[2] ALLYLIC ALCOHOLS OF UNEXPECTED CONFIGURATION BY OXAZABOROLIDINE-CATALYZED REDUCTION OF ALPHA,BETA-UNSATURATED KETONES - AN EXPLANATION-BASED ON MO CALCULATIONS
BACH, J
BERENGUER, R
FARRAS, J
GARCIA, J
MESEGUER, J
VILARRASA, J
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (11) : 2683 - 2686
[3] Highly enantioenriched propargylic alcohols by oxazaborolidine-mediated reduction of acetylenic ketones
Bach, J
Berenguer, R
Garcia, J
Loscertales, T
Vilarrasa, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 9021 - 9025
[4] ASYMMETRIC REDUCTION OF KETONES BY USING COMPLEXES OF LITHIUM TETRAHYDRIDOALUMINATE(III) WITH 1,4=3,6-DIANHYDRO-D-MANNITOL AND "1,3=4,6-DI-O-BENZYLIDENE-D-MANNITOL
BAGGETT, N
STRIBBLEHILL, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10): : 1123 - 1126
[5] THE MECHANISM OF ASYMMETRIC HYDROGENATION - CHIRAL BIS(DIPHENYLPHOSPHINO)-ALPHA-PHENYLALKANE COMPLEXES IN CATALYTIC AND STRUCTURAL STUDIES
BROWN, JM
MURRER, BA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (04): : 489 - 497
[6] NEW CHIRAL PHOSPHOLANES - SYNTHESIS, CHARACTERIZATION, AND USE IN ASYMMETRIC HYDROGENATION REACTIONS
BURK, MJ
FEASTER, JE
HARLOW, RL
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (07) : 569 - 592
[7] HIGHLY ENANTIOSELECTIVE HYDROGENATION OF BETA-KETO-ESTERS UNDER MILD CONDITIONS
BURK, MJ
HARPER, TGP
KALBERG, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) : 4423 - 4424
[8] ISOLATION OF RACEMIC 2,4-PENTANEDIOL AND 2,5-HEXANEDIOL FROM COMMERCIAL MIXTURES OF RACEMIC AND MESO ISOMERS BY WAY OF CYCLIC SULFITES
CARON, G
KAZLAUSKAS, RJ
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (04) : 657 - 664
[9] HIGH-YIELD SYNTHESES OF DILITHIO-DERIVATIVES OF FURAN, THIOPHENE, N-METHYLPYRROLE, 3-METHYLFURAN, AND 3-METHYLTHIOPHEN - APPLICATION OF METHOD TO 2-METHYLFURAN, 2-METHYLTHIOPHEN, 2,5-DIMETHYLFURAN, 2,5-DIMETHYLTHIOPHEN, BENZO[B]FURAN, BENZO[B]THIOPHEN, PYRROLE, AND INDOLE
CHADWICK, DJ
WILLBE, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08): : 887 - 893
[10] CHONG JM, 1995, TETRAHEDRON-ASYMMETR, V6, P409

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