A Diels-Alder approach to the stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines

被引：55

作者：

Sales, M ^{[1
]}

Charette, AB ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 26期

关键词：

D O I：

10.1021/ol052436v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines was achieved from oxidative cleavage of 2-aza-bicyclo-[2.2.2]octene Diels-Alder adducts derived from N-protected 2-methyl-1,2-dihydropyridine. A chiral auxiliary mediated asymmetric synthesis of the pentasubstituted piperidine is also demonstrated. This methodology incorporates orthogonal protecting groups, thus providing a piperidine scaffold with easily modified points of diversity.

引用

页码：5773 / 5776

页数：4

共 50 条

[1] The Evans Aldol-Prins cyclization: a general and stereoselective method for the synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans
Alvarez-Mendez, Sergio J.
Garcia, Celina
Martin, Victor S.
CHEMICAL COMMUNICATIONS, 2016, 52 (16) : 3380 - 3383
[2] SYNTHESIS AND DIELS-ALDER REACTIVITY OF 2,3,5,6-TETRAMETHYLIDENENORBORNANE
PILET, O
VOGEL, P
HELVETICA CHIMICA ACTA, 1981, 64 (08) : 2563 - 2570
[3] MULTICOMPONENT REACTION FOR THE SYNTHESIS OF 1,2,3,4,6-PENTASUBSTITUTED PIPERIDINES CATALYZED BY NIS
Liu Pengpeng
HETEROCYCLES, 2021, 102 (08) : 1563 - 1569
[4] 3(5)-(2-hydroxyphenyl)-5(3)-styrylpyrazoles: Synthesis and Diels-Alder transformations
Silva, VLM
Silva, AMS
Pinto, DCGA
Cavaleiro, JAS
Elguero, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (21) : 4348 - 4356
[5] One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions
Mahmood, Adeem
Suarez, Jose Ramon
Thomas, Stephen P.
Aggarwal, Varinder K.
TETRAHEDRON LETTERS, 2013, 54 (01) : 49 - 51
[6] ANTHRACYCLINONES .2. SYNTHESIS OF (+/-)-4-DEMETHOXYDAUNOMYCINONE BY DOUBLE DIELS-ALDER ADDITIONS TO 2,3,5,6-TETRAMETHYLIDENE-7-OXANORBORNANE
BESSIERE, Y
VOGEL, P
HELVETICA CHIMICA ACTA, 1980, 63 (01) : 232 - 243
[7] N-(2,3,4,5,6-PENTAFLUOROPHENYL)MALEIMIDE AS A POWERFUL DIENOPHILE IN DEAROMATIZING DIELS-ALDER REACTIONS
Hagiwara, Koichi
Iwatsu, Masafumi
Urabe, Daisuke
Inoue, Masayuki
HETEROCYCLES, 2015, 90 (01) : 659 - 672
[8] Saccharin-catalyzed multicomponent cascade reactions for the synthesis of 1,2,3,4,6-pentasubstituted piperidines
Xia, Zihao
Wu, Lisha
Yan, Shiqiang
Zhao, Hanqing
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (06) : 1070 - 1075
[9] Synthesis and Investigation of 2,3,5,6-Tetra-(1H-tetrazol-5-yl)pyrazine Based Energetic Materials
Witkowski, Tomasz G.
Richardson, Paul
Gabidullin, Bulat
Hu, Anguang
Murugesu, Muralee
CHEMPLUSCHEM, 2018, 83 (11): : 984 - 990
[10] Synthesis and highly selective Diels-Alder cycloadditions of the new dienes N-substituted 2,3,5,6-tetrahydrobenzoxazol-2-ones
Martínez, R
Jiménez-Vázquez, HA
Delgado, F
Tamariz, J
TETRAHEDRON, 2003, 59 (04) : 481 - 492

← 1 2 3 4 5 →