Asymmetric synthesis of 1,3-aminoketals

被引：14

作者：

Bariau, A ^{[1
]}

Canet, JL ^{[1
]}

Chalard, P ^{[1
]}

Troin, Y ^{[1
]}

机构：

[1] Univ Clermont Ferrand, Ecole Natl Super Chim Clermont Ferrand, Lab Chim Heterocycles & Glucides, F-63174 Aubiere, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 22期

关键词：

D O I：

10.1016/j.tetasy.2005.09.024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric synthesis of alpha-chiral 1,3-aminoketals 1, useful chiral building blocks for piperidine preparation, was achieved in seven steps involving highly diastereoselective 1,4-addition of Davies' lithium amide to an alpha,beta-unsaturated ester. Problems of partial racernization observed during transformation of the ester moiety into a keto function, via a Weinreb amide, were solved using non-conventional experimental conditions. This procedure allowed the preparation of the title compounds in > 90% enantiomeric excess. (c) 2005 Elsevier Ltd. All rights reserved.

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收藏

页码：3650 / 3660

页数：11

相关论文

共 68 条

[21] ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS [J].

DAVIES, SG ;

ICHIHARA, O ;

WALTERS, IAS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (09) :1141-1147

[22] ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].

DAVIES, SG ;

ICHIHARA, O .

TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186

[23]

DAVIES SG, 1995, SYNLETT, P700

[24] Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived δ-amino β-ketoesters.: Formal synthesis of pseudodistomin B triacetate [J].

Davis, FA ;

Zhang, JY ;

Li, YX ;

Xu, H ;

DeBrosse, C .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5413-5419

[25] Asymmetric synthesis of α-substituted β-amino ketones from sulfinimines (N-sulfinyl imines).: Synthesis of the indolizidine alkaloid (-)-223A [J].

Davis, FA ;

Yang, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8398-8407

[26] Asymmetric synthesis of β-amino carbonyl compounds with N-sulfinyl β-amino Weinreb amides [J].

Davis, FA ;

Nolt, MB ;

Wu, YZ ;

Prasad, KR ;

Li, DY ;

Yang, B ;

Bowen, K ;

Lee, SH ;

Eardley, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2184-2190

[27] Direct asymmetric synthesis of β-amino ketones from sulfinimines (N-sulfinylimines).: Synthesis of (-)-indolizidine 209B [J].

Davis, FA ;

Yang, B .

ORGANIC LETTERS, 2003, 5 (26) :5011-5014

[28]

DAVIS FA, 2002, ORG LETT, V4, P925

[29] DIASTEREOSELECTIVE ALKYLATION OF 3-AMINOBUTANOIC ACID IN THE 2-POSITION [J].

ESTERMANN, H ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1988, 71 (07) :1824-1839

[30] An olefination entry for the synthesis of enantiopure α,ω-diaminodicarboxylates and azabicyclo[X.Y.0] alkane amino acids [J].

Gosselin, F ;

Lubell, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7463-7471

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