Enantioselective addition of organometallic compounds to 3,4-dihydroisoquinoline in the presence of oxazoline derivatives:: synthesis of (R)-(+)- and (S)-(-)-salsolidine

被引：14

作者：

Chrzanowska, M ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(02)00653-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The (R)- and (S)-enantiomers of salsolidine, 2, were prepared in good yield and moderate enantioselectivity (33 and 27% e.e., respectively) by the addition of methyllithium to 6,7-dimethoxy-3,4-dihydroisoqiunoline 1 in the presence of the chiral oxazoline ligands 4 and 10. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2497 / 2500

页数：4

共 25 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2] Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines [J].

Arrasate, S ;

Lete, E ;

Sotomayor, N .

TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2077-2082

[3] CHEMICAL CORRELATION OF THE ABSOLUTE CONFIGURATIONS OF SALSOLIDINE, SALSOLINE, AND CALYCOTOMINE WITH THE AMINO-ACIDS [J].

BATTERSBY, AR ;

EDWARDS, TP .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (MAR) :1214-1221

[4] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[5]

Braunstein P, 2001, ANGEW CHEM INT EDIT, V40, P680, DOI 10.1002/1521-3773(20010216)40:4<680::AID-ANIE6800>3.0.CO

[6]

2-0

[7] Transformation of (+)-thiomicamine into a new ligand for the enantioselective addition of methyllithium to prochiral imines [J].

Brózda, D ;

Chrzanowska, M ;

Gluszynska, A ;

Rozwadowska, MD .

TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4791-4796

[8]

BUSSCHEHUNNEFELD CV, 1992, HELV CHIM ACTA, V75, P438

[9] Enantioselective addition of organolithium reagents to 3,4-dihydroisoquinoline in the presence of (-)-sparteine as an external ligand. Application for the synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Sokolowska, J .

TETRAHEDRON-ASYMMETRY, 2001, 12 (10) :1435-1440

[10]

CLAUSS K, 1968, LIEBIGS ANN CHEM, V711, P19

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