Organocatalytic Enantioselective Synthesis of 6‐Aryl‐5, 6‐dihydrophenanthridines by a Modified Pictet–Spengler Reaction of Biphenyl‐2‐amines and Aromatic Aldehydes. Issue 14 (10th April 2017)

• Record Type: Journal Article
• Authors: Wang, Chaoceng; An, Dong; Guan, Xukai; Fan, Yansen; Liu, Guofeng; Zhang, Guangliang; Zhang, Suoqin
• Is Part Of: European journal of organic chemistry. Issue 14(2017)
• Page Start: 1865
• Page End: 1869
• Publication Date: 2017-04-10
• Subjects: Asymmetric synthesis -- Enantioselectivity -- Fused‐ring systems -- Nitrogen heterocycles -- Organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700185
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A straightforward approach to the enantioselective synthesis of chiral 5, 6‐dihydrophenanthridines was developed. A series of chiral 6‐aryl‐5, 6‐dihydrophenanthridines were obtained through an organocatalytically modified Pictet–Spengler reaction of biphenyl‐2‐amines and aromatic aldehydes. In the reaction, H8 ‐BINOL‐derived chiral imidodiphosphoric acid exhibited strong stereocontrolling and catalytic activities to afford the desired 6‐aryl‐5, 6‐dihydrophenanthridines in high yields (up to 98 %) with high enantioselectivities (up to 99 % ee ). Abstract : An enantioselective Pictet–Spengler reaction of biphenyl‐2‐amines and aromatic aldehydes is realized by using H8 ‐BINOL‐derived chiral imidodiphosphoric acid. Chiral 6‐aryl‐5, 6‐dihydrophenanthridines are obtained in up to 98 % yields with up to 99 % ee .