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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
Author(s) -
Tietze Lutz F.,
Burkhardt Olaf,
Henrich Marielouise
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970718
Subject(s) - regioselectivity , chemistry , intramolecular force , benzazepines , benzazepine , acylation , alcohol , halide , heck reaction , alkylation , medicinal chemistry , substrate (aquarium) , organic chemistry , catalysis , palladium , oceanography , geology
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.