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Et 3 B/Et 2 AlCl/O 2 ‐Mediated Radical Coupling Reaction between α‐Alkoxyacyl Tellurides and 2‐Hydroxybenzaldehyde Derivatives
Author(s) -
Nagatomo Masanori,
Zhang Keshu,
Fujino Haruka,
Inoue Masayuki
Publication year - 2020
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.202001090
Subject(s) - chemistry , stereocenter , reagent , telluride , adduct , coupling reaction , medicinal chemistry , photochemistry , organic chemistry , catalysis , enantioselective synthesis
A newly devised radical‐based strategy enabled coupling between multiply oxygenated α‐alkoxyacyl tellurides and 2‐hydroxybenzaldehyde derivatives. A reagent combination of Et 3 B, Et 2 AlCl, and O 2 promoted the formation of the α‐alkoxy carbon radical from the α‐alkoxyacyl telluride and the addition of the radical to the carbonyl group of 2‐hydroxybenzaldehyde. The reaction chemo‐ and stereoselectively forged the hindered C−C bond between two oxygen‐functionalized carbons at ambient temperature. The method was applied to the preparation of 12 coupling adducts with three to six contiguous stereocenters and to the concise synthesis of an antitumor compound, LLY‐283.