Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides. Issue 35 (31st August 2017)

• Record Type: Journal Article
• Authors: Gharui, Chandan; Singh, Shreya; Pan, Subhas Chandra
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 35(2017)
• Page Start: 7272
• Page End: 7276
• Publication Date: 2017-08-31
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01766a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first organocatalytic asymmetric [4 + 2]-cycloaddition reaction between acyclic enecarbamates with in situ generated ortho -quinone methides has been developed using chiral phosphoric acids as catalysts. Abstract : The first organocatalytic asymmetric reaction of acyclic enecarbamates with o -quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2, 3, 4-trisubstituted chroman products.