Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations

被引:39
作者
García, E [1 ]
Arrasate, S [1 ]
Ardeo, A [1 ]
Lete, E [1 ]
Sotomayor, N [1 ]
机构
[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain
关键词
D O I
10.1016/S0040-4039(00)02319-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3-OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%). (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1511 / 1513
页数:3
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