Diastereodivergent aldol reactions of β-alkoxy ethyl ketones:: Modular access to (1,4)-syn and -anti polypropionates

被引：23

作者：

Arikan, Fatih ^{[2
]}

Li, Jun ^{[2
]}

Menche, Dirk ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Dept Organ Chem, INF 270, D-69120 Heidelberg, Germany

[2] Helmholtz Zentrum Infekt Forsch Med Chem, D-38124 Braunschweig, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 16期

关键词：

D O I：

10.1021/ol801292t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric substrate-controlled aldol reactions of ethyl ketones of type 4 with aldehyde 3 are reported. Modular access to all possible syn-and ant aldol products was obtained by careful choice of reaction conditions. To achieve good selectivities in this diastereodivergent approach, selection of the protective group on the beta-oxygen of the enolate (R-2) was of critical importance.

引用

页码：3521 / 3524

页数：4

共 40 条

[1]

[Anonymous], 1997, ORG REACT

[2] Asymmetric solid-phase synthesis of 6,6-spiroketals [J].

Baran, O ;

Sommer, S ;

Waldmann, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) :3195-3199

[3]

Braun M., 2004, MODERN ALDOL REACTIO, P1

[4] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].

DANDA, H ;

HANSEN, MM ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181

[5] High 1,5-anti stereoinduction in boron-mediated aldol reactions of methyl ketones [J].

Dias, LC ;

Baú, RZ ;

de Sousa, MA ;

Zukerman-Schpector, J .

ORGANIC LETTERS, 2002, 4 (24) :4325-4327

[6] 1,5-asymmetric induction in boron-mediated β-alkoxy methyl ketone aldol addition reactions [J].

Evans, DA ;

Côté, B ;

Coleman, PJ ;

Connell, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10893-10898

[7] REVERSAL OF ALDEHYDE DIASTEREOFACIAL SELECTIVITY IN A METHYL KETONE ALDOL REACTION - APPLICATION TO THE SYNTHESIS OF THE CALYCULIN SPIROKETAL [J].

EVANS, DA ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (43) :6129-6132

[8] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC RUTAMYCIN-B [J].

EVANS, DA ;

NG, HP ;

RIEGER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11446-11459

[9] DOUBLE STEREODIFFERENTIATING ALDOL REACTIONS - THE DOCUMENTATION OF PARTIALLY MATCHED ALDOL BOND CONSTRUCTIONS IN THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].

EVANS, DA ;

DART, MJ ;

DUFFY, JL ;

RIEGER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9073-9074

[10] A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes [J].

Evans, DA ;

Dart, MJ ;

Duffy, JL ;

Yang, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4322-4343

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