Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine

被引：43

作者：

Chen, CY ^{[1
]}

Reamer, RA ^{[1
]}

机构：

[1] Merck Res Labs, Proc Res Dept, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol990608g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient enantioselective synthesis of sertraline, an antidepressant, utilizing anionic imine ring closure is described.

引用

页码：293 / 294

页数：2

共 15 条

[1] Asymmetric total synthesis of (+)-tolterodine, a new muscarinic receptor antagonist, via copper-assisted asymmetric conjugate addition of aryl Grignard reagents to 3-phenyl-prop-2-enoyl-oxazolidinones
Andersson, PG
Schink, HE
Österlund, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 8067 - 8070
[2] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
Bloch, R
[J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
[3] A CATALYTIC ENANTIOSELECTIVE SYNTHETIC ROUTE TO THE IMPORTANT ANTIDEPRESSANT SERTRALINE
COREY, EJ
GANT, TG
[J]. TETRAHEDRON LETTERS, 1994, 35 (30) : 5373 - 5376
[4] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond
Enders, D
Reinhold, U
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1895 - 1946
[5] Representation of organic iodide from correspondent bromides and chlorides.
Finkelstein, H
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1910, 43 : 1528 - 1532
[6] Lewis acid promoted conjugate addition of vinylmagnesium bromide to chiral alpha,beta-unsaturated N-acyl oxazolidinones
Han, YL
Hruby, VJ
[J]. TETRAHEDRON LETTERS, 1997, 38 (42) : 7317 - 7320
[7] LITHIUM-INITIATED IMIDE FORMATION - A SIMPLE METHOD FOR N-ACYLATION OF 2-OXAZOLIDINONES AND BORNANE-2,10-SULTAM
HO, GJ
MATHRE, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) : 2271 - 2273
[8] KOE BK, 1983, J PHARMACOL EXP THER, V226, P686
[9] LIN J, 1998, TETRAHEDRON LETT, V39, P5373
[10] ASYMMETRIC 1,4-ADDITION OF ORGANOCUPRATES TO CHIRAL ALPHA,BETA-UNSATURATED N-ACYL-4-PHENYL-2-OXAZOLIDINONES - A NEW APPROACH TO THE SYNTHESIS OF CHIRAL BETA-BRANCHED CARBOXYLIC-ACIDS
NICOLAS, E
RUSSELL, KC
HRUBY, VJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) : 766 - 770

← 1 2 →