Enantioselective Organocatalyzed Formal [4+2] Cycloaddition of Ketimines with Allenoates: Easy Access to a Tetrahydropyridine Framework with a Chiral Tetrasubstituted Stereogenic Carbon Center | Zendy

Takizawa Shinobu | Zendy; Arteaga Fernando Arteaga | Zendy; Yoshida Yasushi | Zendy; Suzuki Michitaka | Zendy; Sasai Hiroaki | Zendy

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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 .

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