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Enantioselective Organocatalyzed Formal [4+2] Cycloaddition of Ketimines with Allenoates: Easy Access to a Tetrahydropyridine Framework with a Chiral Tetrasubstituted Stereogenic Carbon Center
Author(s) -
Takizawa Shinobu,
Arteaga Fernando Arteaga,
Yoshida Yasushi,
Suzuki Michitaka,
Sasai Hiroaki
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300244
Subject(s) - stereocenter , enantioselective synthesis , chemistry , cycloaddition , organocatalysis , asymmetric carbon , formal synthesis , stereochemistry , catalysis , organic chemistry , optically active
Enantioselective organocatalytic synthesis of tetrahydropyridines bearing a chiral tetrasubstituted carbon stereogenic center has been achieved. The spiro‐type monoaryl phosphine catalyst, ( R )‐SITCP, was found to promote the formal [4+2] cycloaddition of saccharin‐derived ketimines and α‐methyl allenoate to afford the corresponding six‐membered N‐heterocycles in high yields and excellent regioselectivities with up to 93% ee .