Chiral diamines for asymmetric synthesis: an efficient RCM construction of the ligand core of (-)- and (+)-sparteine

被引：23

作者：

Danieli, B

Lesma, G

Passarella, D

Sacchetti, A

Silvani, A

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Univ Milan, CISI, I-20133 Milan, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 42期

关键词：

RCM reactions; asymmetric synthesis; chiral ligands; sparteine;

D O I：

10.1016/j.tetlet.2005.08.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient RCM-based approach was applied to the total asymmetric synthesis of a tricyclic diamine and, formally, of its enantiomer, widely known as efficient and versatile chiral ligands of the sparteine-like type. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7121 / 7123

页数：3

相关论文

共 28 条

[1] Asymmetric cyclization of achiral olefinic organolithiums controlled by a stereogenic lithium: Intramolecular carbolithiation in the presence of (-)-sparteine [J].

Bailey, WF ;

Mealy, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6787-6788

[2]

Basu A, 2002, ANGEW CHEM INT EDIT, V41, P717

[3] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[4] Highly enantiopure C1-symmetric cis-piperidine-3,5-dimethanol monoacetates by enzymatic asymmetrization [J].

Danieli, B ;

Lesma, G ;

Passarella, D ;

Silvani, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3492-3496

[5] Total enantioselective synthesis of (-)-cytisine [J].

Danieli, B ;

Lesma, G ;

Passarella, D ;

Sacchetti, A ;

Silvani, A ;

Virdis, A .

ORGANIC LETTERS, 2004, 6 (04) :493-496

[6] Synthesis of enantiopure diamine ligands related to sparteine, via scandium triflate-catalyzed imino Diels-Alder reactions [J].

Danieli, B ;

Lesma, G ;

Passarella, D ;

Piacenti, P ;

Sacchetti, A ;

Silvani, A ;

Virdis, A .

TETRAHEDRON LETTERS, 2002, 43 (40) :7155-7158

[7] A readily-accessible (+)-sparteine surrogate [J].

Dearden, MJ ;

Firkin, CR ;

Hermet, JPR ;

O'Brien, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11870-11871

[8]

Deiters A, 2000, ANGEW CHEM INT EDIT, V39, P2105, DOI 10.1002/1521-3773(20000616)39:12<2105::AID-ANIE2105>3.0.CO

[9]

2-X

[10] ASYMMETRIC ADDITION OF ORGANOLITHIUM REAGENTS TO IMINES [J].

DENMARK, SE ;

NAKAJIMA, N ;

NICAISE, OJC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8797-8798