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Catalytic Enantioselective Synthesis of Tetrahydroisoquinolines and Their Analogues Bearing a C4 Stereocenter: Formal Synthesis of (+)‐(8 S ,13 R )‐Cyclocelabenzine
Author(s) -
Chen Zhilong,
Wang Zhaobin,
Sun Jianwei
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301065
Subject(s) - stereocenter , enantioselective synthesis , transformation (genetics) , chemistry , computer science , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , gene
A one‐pot wonder : 1,2,3,4‐Tetrahydroisoquinolines with a C4 stereocenter can be formed by using a one‐pot multicomponent chiral phosphoric acid catalyzed transformation of a mixture of oxetane‐tethered benzaldehydes, amines, and the dimethyl ester derivative of the Hantzsch ester (see scheme). This transformation can be used to prepare the spermidine alkaloid (+)‐(8 S ,13 R )‐cyclocelabenzine.