Quinine synthesis studies:: A radical-ionic annulation via mn-mediated addition to chiral N-acylhydrazones

被引：25

作者：

Korapala, Chandra Sekhar ^{[1
]}

Qin, Jun ^{[1
]}

Friestad, Gregory K. ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 21期

关键词：

D O I：

10.1021/ol7017938

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A radical-ionic annulation approach to functionalized perhydroisoquinolines involving Mn-mediated coupling of alkyl iodides and chiral N-acylhydrazones was achieved using only 1.25 equiv of the alkyl iodide. Application of this reaction to alkene-containing substrates en route to quinine offered modest yields, decreasing on scaleup. Control experiments revealed that the alkene interfered with the coupling reaction. A revised approach involving prior oxidation of the alkene offered 93% yield in the Mn-mediated coupling, with the adduct obtained as a single diastereomer.

引用

收藏

页码：4243 / 4246

页数：4

相关论文

共 45 条

[1] Dialkylzinc mediated radical additions to chiral N-enoyloxazolidinones in the presence of benzaldehyde.: Mechanistic investigation, structural characterization of the resulting γ-lactones [J].

Bazin, S ;

Feray, L ;

Vanthuyne, N ;

Bertrand, MP .

TETRAHEDRON, 2005, 61 (17) :4261-4274

[2] Synthesis and selective transformation of nitrogen-containing compounds via radical pathways [J].

Bertrand, M ;

Feray, L ;

Gastaldi, S .

COMPTES RENDUS CHIMIE, 2002, 5 (10) :623-638

[3] A novel total synthesis of (±)-aspidospermidine [J].

Callaghan, O ;

Lampard, C ;

Kennedy, AR ;

Murphy, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :995-1001

[4]

Chatterjee A, 1997, INDIAN J CHEM B, V36, P121

[5] A free radical Mannich type reaction:: selective α-CH aminomethylation of ethers by Ti(III)/t-BuOOH system under aqueous acidic conditions [J].

Clerici, Angelo ;

Cannella, Rosalba ;

Pastori, Nadia ;

Panzeri, Walter ;

Porta, Ombretta .

TETRAHEDRON, 2006, 62 (25) :5986-5994

[6] Highly diastereoselective indium-mediated allylation of chiral hydrazones [J].

Cook, GR ;

Maity, BC ;

Kargbo, R .

ORGANIC LETTERS, 2004, 6 (11) :1741-1743

[7] Domino 1,4-addition/carbocyclization reaction through a radical-polar crossover reaction [J].

Denes, F ;

Chemla, F ;

Normant, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (34) :4043-4046

[8]

Ding H, 2006, HETEROCYCLES, V70, P185

[9] Diastereoselective intermolecular addition of the 1,3-dioxolanyl radical to N-acyl aldohydrazones.: Asymmetric synthesis of α-amino acid derivatives [J].

Fernández, M ;

Alonso, R .

ORGANIC LETTERS, 2003, 5 (14) :2461-2464

[10] Dual activation in asymmetric allylsilane addition to chiral N-acylhydrazones:: Method development, mechanistic studies, and elaboration of homoallylic amine adducts [J].

Friestad, GK ;

Korapala, CS ;

Ding, H .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :281-289

← 1 2 3 4 5 →