Enantioselective Thiourea‐Catalyzed Acyl‐Mannich Reactions of Isoquinolines | Zendy

Taylor Mark S. | Zendy; Tokunaga Norihito | Zendy; Jacobsen Eric N. | Zendy

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Enantioselective Thiourea‐Catalyzed Acyl‐Mannich Reactions of Isoquinolines

Author(s) -

Taylor Mark S.,

Tokunaga Norihito,

Jacobsen Eric N.

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200502277

Subject(s) - enantioselective synthesis , thiourea , chemistry , catalysis , mannich reaction , organic chemistry , combinatorial chemistry , organocatalysis , chloroformate

Inexpensive aromatic feedstocks are substrates for highly enantioselective acylative Mannich reactions catalyzed by a thiourea chiral hydrogen‐bond donor 1 . This methodology provides access to useful 1‐substituted dihydroisoquinolines (see scheme; TrocCl=2,2,2‐trichloroethyl chloroformate, TBS= tert ‐butyldimethylsilyl), which serve as precursors to enantioenriched 1‐substituted tetrahydroisoquinolines.

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