Asymmetric synthesis of functionalized 1,2,3,4-tetrahydroquinolines

被引：36

作者：

Gallou-Dagommer, I ^{[1
]}

Gastaud, P ^{[1
]}

RajanBabu, TV ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 13期

关键词：

D O I：

10.1021/ol016018b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly enantioselective rhodium-catalyzed asymmetric hydrogenation (> 98% ee) and Sharpless epoxidation (> 90% ee) of o-nitrocinnamyl substrates lead to intermediates that can be transformed into tetrahydroquinoline derivatives, Starting materials are produced in high-yielding Heck reactions of an o-nitroaryl iodide and alpha -acetamidoacrylate or methyl acrylate.

引用

页码：2053 / 2056

页数：4

共 49 条

[41] ELECTRONIC AMPLIFICATION OF SELECTIVITY IN RH-CATALYZED HYDROGENATIONS - D-GLUCOSE-DERIVED LIGANDS FOR THE SYNTHESIS OF D-AMINO-ACIDS OR L-AMINO-ACIDS
RAJANBABU, TV
AYERS, TA
CASALNUOVO, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) : 4101 - 4102
[42] Carbohydrate phosphinites as practical ligands in asymmetric catalysis: Electronic effects and dependence of backbone chirality in Rh-catalyzed asymmetric hydrogenations. Synthesis of R- or S-amino acids using natural sugars as ligand precursors
RajanBabu, TV
Ayers, TA
Halliday, GA
You, KK
Calabrese, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 6012 - 6028
[43] POTENTIAL ANTI-TUMOR AGENTS .37. ORGANO-PHOSPHORUS DERIVATIVES OF 9-ANILINOACRIDINE
REWCASTLE, GW
BAGULEY, BC
CAIN, BF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (10) : 1231 - 1235
[44] SCHMIDT U, 1992, SYNTHESIS-STUTTGART, P487
[45] STEREOCHEMISTRY OF THE RING-OPENING OF CHIRAL EPOXIDES DERIVED FROM ALLYLIC ALCOHOLS HAVING 2 SUBSTITUTED-PHENYL GROUPS
TAKAHASHI, K
OGATA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) : 1877 - 1880
[46] Asymmetric Reissert-type reaction promoted by bifunctional catalyst
Takamura, M
Funabashi, K
Kanai, M
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) : 6327 - 6328
[47] SYNTHESIS OF DIHYDRO-1H-PYRROLO[1,2-A]INDOLES AND TETRAHYDROPYRIDO[1,2-A]INDOLES VIA A MODIFIED MADELUNG REACTION
VERBOOM, W
ORLEMANS, EOM
BERGA, HJ
SCHELTINGA, MW
REINHOUDT, DN
[J]. TETRAHEDRON, 1986, 42 (18) : 5053 - 5064
[48] SYNTHESIS OF THE LEFT-HAND SEGMENT OF THE ANTI-TUMOR AGENT CC-1065
WIERENGA, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) : 5621 - 5623
[49] YASUZAWA T, 1995, CHEM PHARM BULL, V43, P378

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