Synthesis of enantiopure 3-alkyl-perhydroazepines by diastereoselective 7-endo-radical cyclisation on a chiral 1,3-perhydrobenzoxazine derivative

被引：9

作者：

Andrés, C ^{[1
]}

Duque-Soladana, JP ^{[1
]}

Iglesias, JM ^{[1
]}

Pedrosa, R ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 12期

关键词：

asymmetric synthesis; radical cyclisations; perhydroazepines; stereoselective synthesis;

D O I：

10.1016/S0040-4039(99)00119-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Competitive alkyl radical 6-exo/7-endo cyclisation on alpha,beta-unsaturated amides derived from chiral perhydrobenzoxazines are controlled by the alkene substitution pattern. Stereocontrol leading to 7-endo regioisomers is considerably higher and allows to prepare enantiopure hexahydroazepine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2421 / 2424

页数：4

共 25 条

[1] Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer
Amat, M
Pshenichnyi, G
Bosch, J
Molins, E
Miravitlles, C
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (11) : 3091 - 3094
[2] Diastereoselective 5-exo-trig radical cyclisation on N-acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines
Andres, C
DuqueSoladana, JP
Iglesias, JM
Pedrosa, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (50) : 9085 - 9086
[3] [Anonymous], COMPREHENSIVE HETERO
[4] 2,3-DISUBSTITUTED TETRAHYDROFURAN SYNTHESIS VIA RADICAL AND ANIONIC CYCLIZATION
BURKE, SD
JUNG, KW
[J]. TETRAHEDRON LETTERS, 1994, 35 (32) : 5837 - 5840
[5] TETRAHYDROPYRAN SYNTHESIS VIA RADICAL CYCLIZATION - A SYSTEMATIC STUDY OF SUBSTITUENT EFFECTS
BURKE, SD
RANCOURT, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) : 2335 - 2336
[6] NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS
CABRI, W
CANDIANI, I
COLOMBO, M
FRANZOI, L
BEDESCHI, A
[J]. TETRAHEDRON LETTERS, 1995, 36 (06) : 949 - 952
[7] COBALT(II) CHLORIDE-GRIGNARD REAGENT - AN ALTERNATIVE TO TIN HYDRIDE IN ARYL RADICAL CYCLIZATIONS
CLARK, AJ
DAVIES, DI
JONES, K
MILLBANKS, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) : 41 - 42
[8] ARYL RADICAL CYCLIZATIONS - QUINOLINE, ISOQUINOLONE, AND 1-BENZAZEPIN-2-ONE RINGS VIA 6-EXO AND 7-EXO CYCLIZATIONS
CLARK, AJ
JONES, K
MCCARTHY, C
STOREY, JMD
[J]. TETRAHEDRON LETTERS, 1991, 32 (24) : 2829 - 2832
[9] CONFORMATIONALLY CONSTRAINED DIPEPTIDES - SYNTHESIS OF 7,5-FUSED AND 6,5-FUSED BICYCLIC LACTAMS BY STEREOSELECTIVE RADICAL CYCLIZATIONS
COLOMBO, L
DIGIACOMO, M
SCOLASTICO, C
MANZONI, L
BELVISI, L
MOLTENI, V
[J]. TETRAHEDRON LETTERS, 1995, 36 (04) : 625 - 628
[10] Curran D. P., 1996, STEREOCHEMISTRY RADI

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