Regioselective reduction of N-alkyl-3-sulfonyl glutarimides.: Synthesis of 3,4-dihydro-3-tosylpyridin-2-ones

被引:17
作者
Chang, BR [1 ]
Chen, CY [1 ]
Chang, NC [1 ]
机构
[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
D O I
10.1016/S0040-4039(02)00446-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of N-alkyl-3-sulfonyl glutarimides (1) with sodium hydride and then lithium aluminum hydride could gibe regioselective reduced hydroxy piperidones (5) which were further dehydrated to 3,4-dihydro-3-tosylpyridin-2-ones (6) in the presence of boron trifluoride. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3233 / 3235
页数:3
相关论文
共 16 条
[1]   Enantioselective synthesis of (-)-indolizidine 167B [J].
Chalard, P ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC ;
Canet, I .
TETRAHEDRON LETTERS, 1999, 40 (09) :1661-1664
[2]   Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)-lasubine II and (+)-subcosine II [J].
Chalard, P ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC .
TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4361-4368
[3]   An efficient synthesis of N-benzyl-3-sulfonyl glutarimides.: Formal synthesis of the aromatase inhibitor AG-1 [J].
Chang, MY ;
Chang, BR ;
Tai, HM ;
Chang, NC .
TETRAHEDRON LETTERS, 2000, 41 (52) :10273-10276
[4]   A new approach to isoindolobenzazepines via a ring-expansion of isoindoloisoquinoline:: Synthesis of lennoxamine and chilenine [J].
Koseki, Y ;
Kusano, S ;
Sakata, H ;
Nagasaka, T .
TETRAHEDRON LETTERS, 1999, 40 (11) :2169-2172
[5]   Tandem carbophilic addition-N-acyliminium ion cyclization for the synthesis of functionalized pyrrolo[2,1-a]isoquinolones: Key intermediates for the preparation of Erythrina-type alkaloids [J].
Manteca, I ;
Sotomayor, N ;
Villa, MJ ;
Lete, E .
TETRAHEDRON LETTERS, 1996, 37 (43) :7841-7844
[6]   Halide-terminated N-acyliminium ion alkyne cyclizations:: A new construction of carbacephem antibiotics [J].
Metais, E ;
Overman, LE ;
Rodriguez, MI ;
Stearns, BA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9210-9216
[7]   A Kulinkovich entry into tertiary N-acyliminium ion chemistry [J].
Ollero, L ;
Mentink, G ;
Rutjes, FPJT ;
Speckamp, WN ;
Hiemstra, H .
ORGANIC LETTERS, 1999, 1 (09) :1331-1334
[8]   A triple cascade sequence as a strategy for the construction of the erythrinane skeleton [J].
Padwa, A ;
Hennig, R ;
Kappe, CO ;
Reger, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1144-1155
[9]   AMIDOALKYLATION OF AROMATICS WITH GLYOXYLIC ACID-GAMMA-LACTAM ADDUCTS - 2-PYRROLIDINONE, PYROGLUTAMIC ACID AMIDE AND ESTER [J].
ROTH, E ;
ALTMAN, J ;
KAPON, M ;
BENISHAI, D .
TETRAHEDRON, 1995, 51 (03) :801-810
[10]   INTRAMOLECULAR REACTIONS OF N-ACYLIMINIUM INTERMEDIATES [J].
SPECKAMP, WN ;
HIEMSTRA, H .
TETRAHEDRON, 1985, 41 (20) :4367-4416