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Direct Catalytic Asymmetric Mannich‐Type Reactions of N ‐(2‐Hydroxyacetyl)pyrrole as an Ester‐Equivalent Donor
Author(s) -
Harada Shinji,
Handa Shinya,
Matsunaga Shigeki,
Shibasaki Masakatsu
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.200501180
Subject(s) - yield (engineering) , indium , catalysis , chemistry , ketone , pyrrole , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
Stretching the limits of the Mannich reaction : A new indium–binol catalyst was used to generate the enolate of the ester‐equivalent donor in situ (see scheme). The donor, an N ‐acylpyrrole, has many similarities to an aromatic ketone, in particular the enolates should have the same coordination mode. Versatile β‐amino‐α‐hydroxy carboxylic acid derivatives were obtained in high yield and ee values.