Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1, 6-addition/transesterification of α-isocyanoacetates with para-quinone methides. Issue 8 (10th February 2020)

• Record Type: Journal Article
• Authors: Zhao, Mei-Xin; Xiang, Juan; Zhao, Zi-Qiang; Zhao, Xiao-Li; Shi, Min
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 8(2020)
• Page Start: 1637
• Page End: 1646
• Publication Date: 2020-02-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02652e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Dihydroquinidine-derived aminophosphine/AgNO3 catalyzed asymmetric tandem 1, 6-addition/transesterification of α-isocyanoacetates with o -hydroxyphenyl-substituted p -QMs was developed. Abstract : A catalytic asymmetric synthesis of 3, 4-dihydrocoumarins with adjacent tertiary–quaternary stereocenters by 1, 6-addition/transesterification cascade reaction of α-isocyanoacetates with ortho -hydroxyphenyl-substituted para -quinone methides ( p -QMs) has been developed. Using a combination of dihydroquinidine-derived aminophosphine and silver nitrate as a binary catalytic system, moderate to good yields, excellent diastereoselectivities (>20 : 1 dr) and good to excellent enantioselectivities (up to 94% ee) were achieved for a wide range of isocyanoacetates and p -QMs.