Stereocontrol in one-pot syntheses of 1,3-diols

被引：9

作者：

Mahrwald, R ^{[1
]}

Ziemer, B ^{[1
]}

机构：

[1] Humboldt Univ, Inst Organ & Bioorgan Chem, D-10155 Berlin, Germany

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

aldol reaction; reduction; stereocontrol; diols;

D O I：

10.1016/S0040-4020(99)00868-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Titanium mediated aldol addition reduction sequence is described for the synthesis of stereodefined 1,3-diols. Diastereochemical control is surprisingly achieved through the careful selection of starting materials used. (C) 1999 Elsevier Science Ltd. All rights reserved. Keywords: aldol reaction, reduction, stereocontrol, diols.

引用

页码：14005 / 14012

页数：8

共 35 条

[1] HYDROXY-DIRECTED REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH CHIRAL ALLYLIC ALCOHOLS [J].

ADAM, W ;

NESTLER, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5041-5049

[2]

[Anonymous], CATALYTIC ASYMMETRIC

[3]

BARLUENGA J, 1981, SYNTHESIS-STUTTGART, P563

[4] CHELATION-CONTROLLED AND NONCHELATION-CONTROLLED REDUCTIONS OF BETA-DICARBONYL COMPOUNDS TO 1,3-DIOLS WITH 3 CHIRAL CENTERS [J].

BARLUENGA, J ;

RESA, JG ;

OLANO, B ;

FUSTERO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1425-1428

[5] Tandem aldol-Tishchenko reactions of lithium enolates: A highly stereoselective method for diol and triol synthesis [J].

Bodnar, PM ;

Shaw, JT ;

Woerpel, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5674-5675

[6] BORON MEDIATED ONE-POT ALDOL-REDUCTION SEQUENCE - ENANTIO AND DIASTEREOSELECTIVE SYNTHESIS OF TYPICAL POLYKETIDE FRAGMENTS [J].

BONINI, C ;

RACIOPPI, R ;

RIGHI, G ;

ROSSI, L .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :173-176

[7]

BRAUN M, 1995, HOUBENWEYL METHODS E, V21, P1603

[8] ASYMMETRIC REDUCTION WITH CHIRAL ORGANOBORANES BASED ON ALPHA-PINENE [J].

BROWN, HC ;

RAMACHANDRAN, PV .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (01) :16-24

[9] THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE HYDROBORATION OF ALLYLSILANES [J].

FLEMING, I ;

LAWRENCE, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3309-3326

[10]

FURSTNER A, 1995, J AM CHEM SOC, V117, P4468

← 1 2 3 4 →