Synthesis of chiral 2-methyl-5,6,7,8-tetrahydroquinolines from naturally occurring monoterpenes

被引：4

作者：

Chelucci, G ^{[1
]}

Orrù, G ^{[1
]}

Soccolini, F ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, Via Vienna 2, I-07100 Sassari, Italy

来源：

ARKIVOC | 2004年

关键词：

chiral tetrahydroquinolines; chiral pyridines; chiral nitrogen heterocycles; Krohnke annulation;

D O I：

10.3998/ark.5550190.0005.e04

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of chiral substituted 2-methylpyridines, in which the pyridine rings are annulated at the 5,6-positions to the chiral frameworks originating from (-)-beta-pinene, (-)- isopinocampheol and (+)- camphor, is reported. Two procedures have been evaluated for their preparation.

引用

页码：44 / 50

页数：7

共 14 条

[1]

BESSIERE.Y, 1970, B SOC CHIM FR, P3103

[2] HYDROBORATION .85. SYNTHESIS AND HYDROBORATION OF (-)-2-PHENYLAPOPINENE - COMPARISON OF MONO(2-PHENYLAPOISOPINOCAMPHEYL)BORANE WITH ITS 2-METHYL AND 2-ETHYL ANALOGS FOR THE CHIRAL HYDROBORATION OF REPRESENTATIVE ALKENES [J].

BROWN, HC ;

WEISSMAN, SA ;

PERUMAL, PT ;

DHOKTE, UP .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1217-1223

[3] Chiral 2,2′-bipyridines, 1,10-phenanthrolines, and 2,2′:6′,2"-terpyridines:: Syntheses and applications in asymmetric homogeneous catalysis [J].

Chelucci, G ;

Thummel, RP .

CHEMICAL REVIEWS, 2002, 102 (09) :3129-3170

[4] PYRIDOANNELATION OF HINDERED KETONES VIA THEIR NITROGEN DERIVATIVES - SYNTHESIS OF 5,6,7,8-TETRAHYDRO-8,9,9-TRIMETHYL-5,8-METHANOQUINOLINES FROM (+)-CAMPHOR [J].

CHELUCCI, G ;

DELOGU, G ;

GLADIALI, S ;

SOCCOLINI, F .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) :1395-1399

[5] Chiral 2-(2-diphenylphosphinophenyl)-5,6,7,8-tetrahydroquinolines: new P-N ligands for asymmetric catalysis [J].

Chelucci, G ;

Saba, A ;

Soccolini, F .

TETRAHEDRON, 2001, 57 (50) :9989-9996

[6] Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms.: Syntheses and applications in asymmetric catalysis [J].

Chelucci, G ;

Orrù, G ;

Pinna, GA .

TETRAHEDRON, 2003, 59 (48) :9471-9515

[7] A 3-STEP PYRIDOANNELATION OF CARBONYL-COMPOUNDS [J].

CHELUCCI, G ;

GLADIALI, S ;

MARCHETTI, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (06) :1761-1765

[8]

Gianini M, 1996, SYNTHESIS-STUTTGART, P702

[9] APOVERBENONE (6,6-DIMETHYLNORPIN-3-EN-2-ONE) - INVESTIGATION INTO ITS PREPARATION BY DEHYDROBROMINATION OF A STERICALLY HINDERED BROMOKETONE [J].

GRIMSHAW, J ;

GRIMSHAW, JT ;

JUNEJA, HR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (01) :50-&

[10] SYNTHESIS USING PYRIDINIUM SALTS .5. SPECIFIC SYNTHESIS OF PYRIDINES AND OLIGOPYRIDINES [J].

KROHNKE, F .

SYNTHESIS-STUTTGART, 1976, (01) :1-24

← 1 2 →