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Synthesis of Chiral Dihydrobenzofurans and Phthalides by Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution: A Strategy for Total Synthesis of Daldinins A, B, and C and Concentricolide
Author(s) -
Fang Lizhen,
Lyu Qinghua,
Lu Chenjuan,
Li Huanhuan,
Liu Saisai,
Han Lili
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600333
Subject(s) - phthalide , chemistry , kinetic resolution , transfer hydrogenation , diastereomer , stereocenter , yield (engineering) , enantioselective synthesis , enantiomer , total synthesis , enantiomeric excess , stereochemistry , asymmetric hydrogenation , noyori asymmetric hydrogenation , resolution (logic) , combinatorial chemistry , organic chemistry , catalysis , materials science , artificial intelligence , ruthenium , computer science , metallurgy
A versatile and efficient strategy for the total synthesis of the anti‐HIV‐1 agent concentricolide and its analogues daldinins A, B, and C has been established. This strategy offers a mild and facile access to these benzo annulated compounds, bearing multiple stereocenters in good yield with 99% enantiomeric excess ( ee ) and 93% diastereomeric excess ( de ) values. Construction of the corresponding syn dihydrobenzofuran and phthalide groups can be achieved in one step by Noyori's asymmetric transfer hydrogenation, via dynamic kinetic resolution.