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Highly Enantioselective Pictet–Spengler Reaction Catalyzed by SPINOL‐Phosphoric Acids
Author(s) -
Huang Dan,
Xu Fangxi,
Lin Xufeng,
Wang Yanguang
Publication year - 2012
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.201103207
Subject(s) - enantioselective synthesis , tryptamines , phosphoric acid , catalysis , pictet–spengler reaction , chemistry , optically active , organic chemistry , combinatorial chemistry , tryptamine , biochemistry
Chiral SPINOL‐phosphoric acids are highly enantioselective catalysts for the asymmetric Pictet–Spengler reaction of N b ‐α‐naphthylmethyl tryptamines with a series of aliphatic and aromatic aldehydes, affording optically active tetrahydro‐β‐carbolines in excellent yields and ee values. The current protocol has been applied in the asymmetric total synthesis of (−)‐harmicine.
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