Pt(II)-catalyzed synthesis of 1,2-dihydropyridines from aziridinyl propargylic esters

被引：43

作者：

Motamed, Massoud ^{[1
]}

Bunnelle, Eric M. ^{[1
]}

Singaram, Surendra W. ^{[1
]}

Sarpong, Richmond ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 11期

关键词：

D O I：

10.1021/ol070658i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pt(II)-catalyzed cycloisomerization of aziridinyl propargylic esters affords 1,2-dihydropyridines with regiodefined installation of substituents. A mild conversion of the 1,2-dihydropyridines to the corresponding substituted pyridines as well as chirality retention from the aziridinyl propargylic ester substrates have been demonstrated.

引用

页码：2167 / 2170

页数：4

共 22 条

[1] Synthesis of 4-functionalized aryl-3,5-diacyl-1,4-dihydropyridines
Bennasar, ML
Roca, T
Monerris, M
Juan, C
Bosch, J
[J]. TETRAHEDRON, 2002, 58 (40) : 8099 - 8106
[2] Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions
Brunner, Bernhard
Stogaitis, Nicole
Lautens, Mark
[J]. ORGANIC LETTERS, 2006, 8 (16) : 3473 - 3476
[3] Aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines with HIO3 and I2O5 in water
Chai, Lingzhi
Zhao, Yankai
Sheng, Qiuju
Liu, Zhong-Quan
[J]. TETRAHEDRON LETTERS, 2006, 47 (52) : 9283 - 9285
[4] Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine
Charette, AB
Grenon, M
Lemire, A
Pourashraf, M
Martel, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) : 11829 - 11830
[5] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF 1-ACYL-2-ALKYL-1,2-DIHYDROPYRIDINES
COMINS, DL
HONG, H
SALVADOR, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) : 7197 - 7199
[6] CORDELL AB, 2003, ALKALOIDS CHEM BIOL, V60
[7] QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS FOR 1,4-DIHYDROPYRIDINE CALCIUM-CHANNEL ANTAGONISTS (NIFEDIPINE ANALOGS) - A QUANTUM CHEMICAL/CLASSICAL APPROACH
GAUDIO, AC
KOROLKOVAS, A
TAKAHATA, Y
[J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (08) : 1110 - 1115
[8] HESSE M, 2003, ALKALOIDS NATURES CU
[9] New entries in Lewis acid Lewis base bifunctional asymmetric catalyst: Catalytic enantioselective Reissert reaction of pyridine derivatives
Ichikawa, E
Suzuki, M
Yabu, K
Albert, M
Kanai, M
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) : 11808 - 11809
[10] Novel catalysts for the Overman rearrangement
Jaunzeme, I
Jirgensons, A
[J]. SYNLETT, 2005, (19) : 2984 - 2986

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