Stereoselective synthesis of the pyrroloisoquinoline ring system

被引：43

作者：

Allin, SM ^{[1
]}

James, SL

Martin, WP

Smith, TAD

Elsegood, MRJ

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] GlaxoSmithKline Pharmaceut, Synthet Chem, Harlow CM19 5AW, Essex, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 22期

关键词：

D O I：

10.1039/b105402n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper we report a facile and stereoselective approach to the pyrroloisoquinoline ring system through the application of N-acyliminium chemistry from readily available non-racemic chiral templates. The stereochemical outcome of the cyclisation reactions has been determined by NOE and X-ray crystallography. We also demonstrate the synthetic potential of our new approach through removal of the pendant hydroxymethyl auxiliary from a product of cyclisation.

引用

页码：3029 / 3036

页数：8

共 25 条

[1] Ahn N. T., 1977, NOUV J CHIM, V1, P61
[2] A facile and highly stereoselective approach to a polycyclic isoindolinone ring system via an N-acyliminium ion cyclization reaction
Allin, SM
Northfield, CJ
Page, MI
Slawin, AMZ
[J]. TETRAHEDRON LETTERS, 1998, 39 (27) : 4905 - 4908
[3] *BRUK AXS INC, 1994, SMART SAINT SOFTW CC
[4] ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN
BURGESS, LE
MEYERS, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) : 9858 - 9859
[5] CHEREST M, 1968, TETRAHEDRON LETT, P219
[6] Dyke S.F., 1981, ALKALOIDS CHEM PHYSL, V18, P1, DOI DOI 10.1016/S1876-0813(08)60236-5
[7] ELIEL EL, 1994, STEREOCHEMISTRY ORGA, P876
[8] EXTARRI B, 1999, SYNLETT, P1486
[9] Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations
García, E
Arrasate, S
Ardeo, A
Lete, E
Sotomayor, N
[J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1511 - 1513
[10] Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions
Groaning, MD
Meyers, AI
[J]. TETRAHEDRON, 2000, 56 (51) : 9843 - 9873

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