4-Piperidones from enantiomerically pure enones. Synthesis of 6-alkylsubstituted 4-oxo-pipecolic acid derivatives

被引：2

作者：

Galley, G ^{[1
]}

Ziemer, B ^{[1
]}

Patzel, M ^{[1
]}

机构：

[1] Humboldt Univ, Inst Chem, D-10115 Berlin, Germany

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1998年 / 340卷 / 06期

关键词：

D O I：

10.1002/prac.19983400608

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The cyclization of the enantiomerically pure alpha,beta-unsaturated ketone 1, an aliphatic aldehyde 3 and ammonia or benzylamine gives diastereoselectively cis-piperidones 4/4'. Although only modest yields were obtained, the presented cyclization has the advantage of being a single step reaction. The products 4 can serve as precursors for all-cis-4-hydroxypiperidones 5 and novel pipecolic acid derivatives 9.

引用

页码：551 / 556

页数：6

共 50 条

[41] Access to enantiomerically pure intermediates for (-)-geosmin synthesis starting from (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methyl-naphthalen-2(3H)-one
Fuhshuku, K
Sugai, T
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (10) : 2267 - 2272
[42] Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver
Ling, TS
Shiu, S
Yang, DY
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (07) : 1459 - 1465
[43] Synthesis of 4-Acetoxyindoles and Related Derivatives by Means of Air Oxidation of 4-Oxo-4,5,6,7-tetrahydroindoles Obtained from Nitroalkenes and Cyclohexane-1,3-diones
Arai, Masaki
Miyauchi, Yayoi
Miyahara, Tadashi
Ishikawa, Teruhiko
Saito, Seiki
SYNLETT, 2009, (01) : 122 - 126
[44] Synthesis and evaluation of antitrypanosomal activity of some thiosemicarbazide derivatives of 1-butyl-6-fluoro-7-morpholino-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Pyrih, Andriy
Berninger, Michael
Gzella, Andrzej
Lesyk, Roman
Holzgrabe, Ulrike
SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1883 - 1891
[45] Silica Sulfuric Acid: An Efficient and Versatile Catalyst for One-Pot Synthesis of Substituted 5-Oxo-1,4,5,6,7,8-hexahydroquinoline Derivatives
Qin, Xin-Ying
Jin, Tong-Shou
Zhou, Zun-Xia
Li, Tong-Shuang
ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (02) : 1179 - 1182
[46] Isolation of enantiomerically pure organometallic palladium compounds: synthesis of the triangles prepared from enantiopure [cis-Pd2(C6H4PPh2)2(NCCH3)4]2+
Koshevoy, Igor O.
Gutierrez-Puebla, Enrique
Lahuerta, Pascual
Monge, Angeles
Ubeda, M. Angeles
Sanau, Mercedes
DALTON TRANSACTIONS, 2009, (16) : 2993 - 2998
[47] SYNTHESIS OF DERIVATIVES OF THIAZOLIDIN-2,4-DIONE AND 2-IMINOTHIAZOLIDIN-4-ONE FROM 6-AMINOCAPROIC ACID
WITKOWSKI, S
CZEREPKO, K
ROSZKOWSKA, W
WOROWSKI, K
ACTA POLONIAE PHARMACEUTICA, 1983, 40 (03): : 309 - 312
[48] MICHAEL ADDITION OF BENZOYLACETONITRILE TO CHIRAL ALPHA-CYANOACRYLATES DERIVED FROM ENANTIOMERICALLY PURE ALPHA-HYDROXYALDEHYDES - SYNTHESIS OF 3-ALKOXYCARBONYL-4-ALKYL-2-AMINO-5-CYANO-6-PHENYL-4H-PYRAN
JIMENEZ, B
MARTIN, N
MARTINEZGRAU, A
SEOANE, C
MARCO, JL
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) : 1381 - 1384
[49] A SHORT SYNTHESIS OF ENANTIOMERICALLY PURE (2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOIC ACID, THE UNUSUAL C-9 AMINO-ACID FOUND IN THE IMMUNOSUPPRESSIVE PEPTIDE CYCLOSPORINE
AEBI, JD
DHAON, MK
RICH, DH
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13): : 2881 - 2886
[50] SYNTHESIS AND PROPERTIES OF THE DERIVATIVES OF 2-ALKYLTHIO-4-OXO-3,4-DIHYDROPYRIDO[2,3-D]PYRIMIDINE-5-CARBOXYLIC ACID AND 2-ALKYLTHIO-4-OXO-1,4-DIHYDROPYRIDO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID
SLADOWSKA, H
BARTOSZKOMALIK, A
ZAWISZA, T
FARMACO, 1990, 45 (01): : 111 - 121

← 1 2 3 4 5 →