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Synlett 2000; 2000(1): 101-103
DOI: 10.1055/s-2000-6450
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Diastereodivergent Approaches to Thiazolo[4,3-a]isoquinoline Systems via Parham-type and N-acyliminium ion Cyclizations

Iñaki Osante* , M. Isabel Collado, Esther Lete, Nuria Sotomayor
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad del País Vasco, Apdo. 644, 48080 Bilbao, Spain; Fax 34-94-4 64 85 00; E-mail: qopleexe@lg.ehu.es
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Publication Date:
31 December 2000 (online)

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Diastereodivergent approaches to thiazolo[4,3-a]isoquinoline systems are described. The sequence reduction - N-acyliminium cyclization of 1-substituted N-phenethylthiazolidinediones afforded stereoselectively the 1,10b-cis derivatives. Alternatively, the tandem Parham cyclization - hydroxyl reduction on the corresponding iodinated thiazolidinediones occurred with complete control of stereoselectivity, leading to the 1,10b-trans diastereomers. Typical yields of the resulting thiazolo[4,3-a]isoquinolines ranged 66-92% with facial diastereoselectivities of > 95 : 5.

thiazoloisoquinolines - lithium iodine exchange - N-acyliminium ion - cyclization - diastereoselectivity

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