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Stereo- and regioselective intramolecular heck reaction of α-amino acid derivatives for the synthesis of enantiopure 3,4-dihydroisoquinolinones

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

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
513 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 presence of PPh~3~, TPAB, and KOAc with excellent diastereoselectivity.

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