ISSN:
0947-3440
Keywords:
Heck reaction, intramolecular
;
α-Amino acids
;
Isoquinolines
;
Palladium
;
Heterocycles
;
Synthesis, enantioselective
;
High pressure
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 PPh3, 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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970718
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