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
Aguilera, B
FernandezMayoralas, A
Jaramillo, C
[J]. TETRAHEDRON, 1997, 53 (16) : 5863 - 5876
[2] Synthesis of a thio-analogue of Lewis X by regioselective opening of cyclic sulfamidates
Aguilera, B
Fernández-Mayoralas, A
[J]. 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
Aguilera, B
FernandezMayoralas, A
[J]. 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
ALKER, D
DOYLE, KJ
HARWOOD, LM
MCGREGOR, A
[J]. 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
Amere, Mukkanti
Lasne, Marie-Claire
Rouden, Jacques
[J]. ORGANIC LETTERS, 2007, 9 (14) : 2621 - 2624
[6] STUDIES ON AMINO-ACIDS AND PEPTIDES .4. 1,2,4-TRIAZINES FROM THIOACYLATED AMINO-ACID ESTERS
ANDERSEN, TP
GHATTAS, ABAG
LAWESSON, SO
[J]. TETRAHEDRON, 1983, 39 (20) : 3419 - 3427
[7] Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B
Angle, SR
Henry, RM
[J]. 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
Atfani, M
Wei, L
Lubell, WD
[J]. ORGANIC LETTERS, 2001, 3 (19) : 2965 - 2968
[9] SN2 reaction of sulfur nucleophiles with hindered sulfamidates:: Enantioselective synthesis of α-methylisocysteine
Avenoza, A
Busto, JH
Jiménez-Osés, G
Peregrina, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) : 1692 - 1695
[10] Stereoselective synthesis of orthogonally protected α-methylnorlanthionine
Avenoza, Alberto
Busto, Jesuus H.
Jimenez-Oses, Gonzalo
Peregrina, Jesus M.
[J]. ORGANIC LETTERS, 2006, 8 (13) : 2855 - 2858

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