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Enantioselective Total Synthesis of Chromanone Lactone Homo‐ and Heterodimers
Author(s) -
Valdomir Guillermo,
Senthilkumar Soundararasu,
Ganapathy Dhandapany,
Zhang Yun,
Tietze Lutz F.
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800619
Subject(s) - enantioselective synthesis , lactone , chemistry , phenol , yield (engineering) , ether , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
A one pot borylation/Suzuki–Miyaura reaction of the 4‐bromochromanone lactones 21 and 23 , respectively, followed by cleavage of the methyl ether moieties gave the homodimeric chromanone lactones 10 and 11 . Reaction of a 1:1 mixture of 21 and 23 under otherwise identical conditions gave a 1:1:2‐mixture of the two homodimers 10 and 11 and the heterodimer 12 . This is the first example of the preparation of a heterodimeric chromanone lactone. For the enantioselective synthesis of the starting material, phenol 17 was transformed into the chromane 18 using a Wacker‐type cyclisation with 99 % ee and 80 % yield.