Enantioselective Organocatalyzed Formal [4+2] Cycloaddition of Ketimines with Allenoates: Easy Access to a Tetrahydropyridine Framework with a Chiral Tetrasubstituted Stereogenic Carbon Center. Issue 4 (16th January 2014)

• Record Type: Journal Article
• Authors: Takizawa, Shinobu; Arteaga, Fernando Arteaga; Yoshida, Yasushi; Suzuki, Michitaka; Sasai, Hiroaki
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 4(2014:Apr.)
• Page Start: 412
• Page End: 415
• Publication Date: 2014-01-16
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201300244
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Enantioselective organocatalytic synthesis of tetrahydropyridines bearing a chiral tetrasubstituted carbon stereogenic center has been achieved. The spiro‐type monoaryl phosphine catalyst, (<italic>R</italic>)‐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% <italic>ee</italic>.</p> </abstract>