A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: a formal synthesis of (S)-coniine from L-norvaline

被引：14

作者：

Karanfil, Abdullah ^{[1
]}

Balta, Berrin ^{[1
]}

Eskici, Mustafa ^{[1
]}

机构：

[1] Celal Bayar Univ, Fac Arts & Sci, Dept Chem, TR-45016 Mansa, Turkey

来源：

TETRAHEDRON | 2012年 / 68卷 / 49期

关键词：

Cyclic sulfamidates; Lithium triethylorthopropiolate; Cyclization; Piperidines; GLYCOSYL AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; LACTAM PRECURSORS; CYCLIC SULFAMATE; FACILE ENTRY; ALPHA; REACTIVITY; DERIVATIVES;

D O I：

10.1016/j.tet.2012.09.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding delta-amino-alpha,beta-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from L-norvaline. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：10218 / 10229

页数：12

共 104 条

[1] Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations [J].

Aguilera, B ;

FernandezMayoralas, A ;

Jaramillo, C .

TETRAHEDRON, 1997, 53 (16) :5863-5876

[2] Synthesis of a thio-analogue of Lewis X by regioselective opening of cyclic sulfamidates [J].

Aguilera, B ;

Fernández-Mayoralas, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2719-2723

[3] Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides [J].

Aguilera, B ;

FernandezMayoralas, A .

CHEMICAL COMMUNICATIONS, 1996, (02) :127-128

[4] THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN [J].

ALKER, D ;

DOYLE, KJ ;

HARWOOD, LM ;

MCGREGOR, A .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :877-880

[5] Highly enantioselective decarboxylative protonation of α-aminomalonates mediated by thiourea Cinchona alkaloid derivatives:: Access to both enantiomers of cyclic and acyclic α-aminoacids [J].

Amere, Mukkanti ;

Lasne, Marie-Claire ;

Rouden, Jacques .

ORGANIC LETTERS, 2007, 9 (14) :2621-2624

[6] STUDIES ON AMINO-ACIDS AND PEPTIDES .4. 1,2,4-TRIAZINES FROM THIOACYLATED AMINO-ACID ESTERS [J].

ANDERSEN, TP ;

GHATTAS, ABAG ;

LAWESSON, SO .

TETRAHEDRON, 1983, 39 (20) :3419-3427

[7] Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B [J].

Angle, SR ;

Henry, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8549-8552

[8] N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates:: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids [J].

Atfani, M ;

Wei, L ;

Lubell, WD .

ORGANIC LETTERS, 2001, 3 (19) :2965-2968

[9] SN2 reaction of sulfur nucleophiles with hindered sulfamidates:: Enantioselective synthesis of α-methylisocysteine [J].

Avenoza, A ;

Busto, JH ;

Jiménez-Osés, G ;

Peregrina, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1692-1695

[10] Stereoselective synthesis of orthogonally protected α-methylnorlanthionine [J].

Avenoza, Alberto ;

Busto, Jesuus H. ;

Jimenez-Oses, Gonzalo ;

Peregrina, Jesus M. .

ORGANIC LETTERS, 2006, 8 (13) :2855-2858

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