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Enantioselective Construction of Chiral 2,3‐ cis ‐Dimethyldihydrobenzofuran with an All‐Carbon Quaternary Center: An Efficient Approach to (+)/(−)‐PI‐220 and (+)‐3‐ epi ‐Furaquinocin C
Author(s) -
Pu LiuYang,
Chen JiQiang,
Li MaoLin,
Li Yao,
Xie JianHua,
Zhou QiLin
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.201500952
Subject(s) - enantioselective synthesis , chemistry , kinetic resolution , intramolecular force , asymmetric hydrogenation , ruthenium , quaternary carbon , catalysis , stereochemistry , palladium , asymmetric carbon , combinatorial chemistry , optically active , medicinal chemistry , organic chemistry
A new strategy for the enantioselective construction of chiral 2,3‐ cis ‐dimethyldihydrobenzofurans has been developed by a ruthenium‐catalyzed asymmetric hydrogenation of racemic α‐aryloxybutanone via dynamic kinetic resolution (DKR), combined with a palladium‐catalyzed intramolecular reductive Heck cyclization. Starting from optically active 2,3‐ cis ‐dimethyldihydrobenzofuran, the natural products (+)/(−)‐PI‐220 and (+)‐3‐ epi ‐furaquinocin C were synthesized in high yields.