Diastereoselective Synthesis of 1-Benzyltetrahydroisoquinoline Derivatives from Amino Acids by 1,4 Chirality Transfer

✍ Scribed by Anna Zawadzka; Andrzej Leniewski; Jan K. Maurin; Krystyna Wojtasiewicz; Aleksandra Siwicka; Dariusz Blachut; Zbigniew Czarnocki

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 239 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200200705

✦ Synopsis

Abstract

L‐Amino acids (L‐Ala, L‐Phe, L‐Val, L‐Pro) were used as a source of chirality in the diastereoselective synthesis of tetrahydroisoquinoline derivatives. The key step was the Pictet−Spengler condensation of ketoamides 4 and 10, which proceeded under very mild conditions. L‐Ala, L‐Phe and L‐Val gave rise the R‐configuration at the newly formed stereogenic center. Surprisingly, L‐Pro gave the opposite result. The stereochemistry of 6d and 12a were established on the basis of X‐ray crystallographic data. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)