Catalytic Enantioselective Synthesis of Tetrahydroisoquinolines and Their Analogues Bearing a C4 Stereocenter: Formal Synthesis of (+)‐(8 S ,13 R )‐Cyclocelabenzine | Zendy

Chen Zhilong | Zendy; Wang Zhaobin | Zendy; Sun Jianwei | Zendy

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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.

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