Catalytic Asymmetric Carbene Insertion Reactions into B−H Bonds Using a Ru(II)‐Pheox Complex | Zendy

Otog Nansalmaa | Zendy; Chanthamath Soda | Zendy; Fujisawa Ikuhide | Zendy; Iwasa Seiji | Zendy

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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.

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