Ru(η1-BH4)(daipena)(diphosphine): Ruthenabicyclic borohydride complexes for asymmetric hydrogenation of ketones and asymmetric formal hydroamination of allylic alcohols under base-free conditions

Ruthenabicyclic complexes bearing a η1-BH4 ligand and exhibiting notable stability under air were developed. These novel Ru complexes were efficient catalyst precursors for asymmetric hydrogenation of simple ketones under base-free conditions or with a small amount of DABCO to afford the correspondi...

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Bibliographic Details
Published in:Tetrahedron 2023-12, Vol.149, p.133705, Article 133705
Main Authors: Ishizaka, Tomohiro, Nakayama, Yuji, Touge, Taichiro, Yuki, Yamato, Matsumura, Kazuhiko, Yurino, Taiga, Ohkuma, Takeshi
Format: Article
Language:English
Subjects:
air
Asymmetric catalysis
Base free
Borohydride
borohydrides
catalysts
enantioselectivity
Hydroamination
Hydrogenation
ligands
Ruthenium
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Summary:Ruthenabicyclic complexes bearing a η1-BH4 ligand and exhibiting notable stability under air were developed. These novel Ru complexes were efficient catalyst precursors for asymmetric hydrogenation of simple ketones under base-free conditions or with a small amount of DABCO to afford the corresponding alcohols with high enantioselectivity (>99 % ee in the best cases). Asymmetric formal hydroamination of allylic alcohols without an addition of base, via a borrowing hydrogenation strategy, was also achieved. A variety of allylic alcohols and amines were applicable to the reaction (>99 % ee in the best cases). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133705