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Catalytic Asymmetric Carbene Insertion Reactions into B−H Bonds Using a Ru(II)‐Pheox Complex
Author(s) -
Otog Nansalmaa,
Chanthamath Soda,
Fujisawa Ikuhide,
Iwasa Seiji
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100034
Subject(s) - chemistry , carbene , insertion reaction , migratory insertion , borane , medicinal chemistry , catalysis , phosphine , yield (engineering) , triphenylphosphine , adduct , amine gas treating , stereochemistry , organic chemistry , materials science , metallurgy
The Ru(II)‐Pheox catalyzed B−H bond insertion reactions of α‐methyl diazoesters with phosphine‐ and amine‐borane adducts were successfully developed. A unique α‐methyl diazoester (dinaphthylenyl diazopropionate) with triphenylphosphine‐borane afforded the highest enantioselectivity (up to 98 % ee ). Moreover, a unique dinaphthylenyl diazophenylacetate was newly synthesized, leading to improved yield and enantioselectivity of the carbene transfer B−H insertion reaction.