✦ LIBER ✦

2-Bis (dimethylamino)phosphinoyl-1-lithio-1, 2, 3, 4-tetrahydroisoquinoline. A highly nucleophilic d1-reagent for the preparation of 1-substituted tetrahydroisoquinolines

✍ Scribed by Dieter Seebach; Masaaki Yoshifuji

Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 284 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640305

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✦ Synopsis

Abstract

The title compound 4 is generated from the phosphoric amide 5 in tetrahydrofuran with butyllithium. The lithium reagent 4 is stable at room temperature; its reactions with electrophiles furnish the products 6–22, 26, 27, see Table 1 and the Scheme. A second alkylation is also possible, see 23–25. The cleavage to tetrahydroisoquinolines is accomplished in refluxing aqueous‐methanolic hydrochloric acid, see Table 2. Phosphinoylation, lithiation, reaction with electrophiles and cleavage constitute an efficient sequence for 1‐alkylation of the isoquinoline nucleus.

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