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Diastereo- and Regioselective Intramolecular Heck Reaction of α-Amino Alcohol Derivatives for the Synthesis of Enantiomerically Pure Isoquinolines and Benzazepines at Ambient and High Pressure

✍ Scribed by Tietze, Lutz F. ;Burkhardt, Olaf ;Henrich, Marielouise

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
751 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Alkylation and acylation of the alkenes 9b, c and 10a, b, which are easily prepared from the corresponding α‐amino alcohols, with 2‐halobenzyl and 2‐halobenzoyl halides respectively, gives 11–15. These compounds cyclize with excellent diastereo‐ and regioselectivity to the enantiomerically pure N‐heterocycles 18–20 in an intramolecular Heck reaction using 5 mol‐% of Pd(OAc)~2~ in the presence of PPh~3~, TPAB and KOAc. Under the same conditions substrate 17 leads to the enantiomerically pure benzazepine 24. The reaction of the bromoarene derivatives 14–15 must be performed under high pressure to give good results.

📜 SIMILAR VOLUMES

Stereo- and regioselective intramolecula
Stereo- and regioselective intramolecular heck reaction of α-amino acid derivatives for the synthesis of enantiopure 3,4-dihydroisoquinolinones
✍ Tietze, Lutz F. ;Burkhardt, Olaf 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 513 KB

## Abstract Acylation of the alkenes 1a–d and 3, easily prepared from the corresponding α‐amino acids, with 2‐iodobenzoyl chloride gives 2a–d and 4 which cyclize to the enantiopure dihydroisoquinolinones 5a–d and 9, resp., in an intramolecular Heck reaction using 5 mol‐ % of Pd(OAc)~2~ in the prese