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Enantioselective Synthesis of ( R )‐Convolutamydine A with New N ‐Heteroarylsulfonylprolinamides
Author(s) -
Nakamura Shuichi,
Hara Noriyuki,
Nakashima Hiroki,
Kubo Koji,
Shibata Norio,
Toru Takeshi
Publication year - 2008
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.200800981
Subject(s) - enantioselective synthesis , aldol reaction , trifluoroacetic acid , isatin , catalysis , chemistry , acetone , organic chemistry , aldol condensation
Unconvoluted synthesis : An enantioselective aldol reaction of acetone with various isatin derivatives, catalyzed by a novel organocatalyst, afforded convolutamydine A derivatives with high enantioselectivity (see scheme, TFA= trifluoroacetic acid). The catalyst loading can be reduced to 0.5 mol % without the loss of enantioselectivity, even though direct aldol reactions between ketones and organocatalysts generally need high catalyst loading.