Aminohydroxylation and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyridines

被引：7

作者：

Chang, Meng-Yang ^{[1
]}

Lin, Chun-Yu

Wu, Tsun-Cheng

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 31期

关键词：

cerium ammonium nitrate; oxidative addition; hydrogenation; 4-aryl-1,2,5,6-tetrahydropyridines; aminohydroxylation; dihydroxylation;

D O I：

10.1016/j.tetlet.2006.05.174

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted 3-amino-4-aryl-4-liydi-oxypiperidines and 4-aryl-3.4-dihvdroxypiperidiiies are synthesized in the modest overall yields starting from the regio- and stereoselective trans-aminohydroxylation and dihydroxylation of 4-aryl-1,15.6-tetrahydropyridines via CAN-mediated oxidative addition and hydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5445 / 5449

页数：5

共 72 条

[51] CAN mediated fragmentation of 1-phenylcycloalkenes: Synthesis of monoacetals of 1,n-dicarbonyl compounds.
Nair, V
Panicker, SB
[J]. TETRAHEDRON LETTERS, 1999, 40 (03) : 563 - 564
[52] NAIR V, 2000, SYNLETT, P156
[53] FUSARIUM-MERISMOIDES CORDA NR-6356, THE SOURCE OF THE PROTEIN-KINASE-C INHIBITOR, AZEPINOSTATIN - TAXONOMY, YIELD IMPROVEMENT, FERMENTATION AND BIOLOGICAL-ACTIVITY
OHSHIMA, S
YANAGISAWA, M
KATOH, A
FUJII, T
SANO, T
MATSUKUMA, S
FURUMAI, T
FUJIU, M
WATANABE, K
YOKOSE, K
ARISAWA, M
OKUDA, T
[J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (06) : 639 - 647
[54] A facile access to polycyclic homo- and heteroaromatic hydrocarbons based on the ceric ammonium nitrate-promoted oxidative addition of 3-aryl-1-[(trimethylsilyl)oxy]cyclohexenes to ethyl vinyl ether
Paolobelli, AB
Ruzziconi, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3364 - 3368
[55] SYNTHESIS AND ABSOLUTE-CONFIGURATIONS OF HEXAHYDRO-NAPHTHOXAZINES AS RIGID CONGENERS OF PHENMETRAZINE
PERRONE, R
BETTONI, G
TORTORELLA, V
[J]. ARCHIV DER PHARMAZIE, 1983, 316 (07) : 617 - 624
[56] Total synthesis of maesanin and analogues
Poigny, S
Guyot, M
Samadi, M
[J]. TETRAHEDRON, 1998, 54 (49) : 14791 - 14802
[57] A stereoselective synthesis of the hexahydroazepine core of (-)-balanol
Raghavan, S
Kumar, CN
[J]. TETRAHEDRON LETTERS, 2006, 47 (10) : 1585 - 1588
[58] CHEMISTRY OF NITRO-COMPOUNDS .6. A NOVEL ONE-POT NITROACETAMIDATION OF OLEFINS USING CERIC AMMONIUM NITRATE-SODIUM NITRITE-ACETONITRILE REAGENT SYSTEM
REDDY, MVR
MEHROTRA, B
VANKAR, YD
[J]. TETRAHEDRON LETTERS, 1995, 36 (27) : 4861 - 4864
[59] Concise, enantiospecific synthesis of (3S,4R)-3-amino-4-ethylpiperidine as partner to a non-fluoroquinolone nucleus
Reilly, M
Anthony, DR
Gallagher, C
[J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2927 - 2930
[60] A highly efficient aminohydroxylation process
Rubin, AE
Sharpless, KB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2637 - 2640

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