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Synthesis of Simple Enantiopure Tetrahydro‐β‐carbolines and Tetrahydroisoquinolines
Author(s) -
Tietze Lutz F.,
Zhou Yifa,
Töpken Enno
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:12<2247::aid-ejoc2247>3.0.co;2-4
Subject(s) - enantiopure drug , enantioselective synthesis , chemistry , enantiomer , tetrahydroisoquinoline , yield (engineering) , stereochemistry , asymmetric hydrogenation , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
Enantioselective hydrogenation of the imines 11−13 , 27 and 30 with the Ru complex ( R , R )‐ 5 led to the tetrahydro‐β‐carbolines (1 S )‐ 14 , (1 R )‐ 21 and (1 S )‐ 22 , and the tetrahydroisoquinoline (1 S )‐ 31 with ee > 95%. By employing ( S , S )‐ 5 the enantiomers are accessible. The imines 11−12 and 27 were obtained by oxidation of racemic 14 , 21 and 22 with KMnO 4 in > 58% yield.