Asymmetric Ir-catalyzed hydrogenation of 4-R-1,3-dihydro-2H-1,5-benzodiazepin-2-ones using a novel phosphoramidite ligand

Journal Article · Mon Jul 15 00:00:00 EDT 2019 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-019-2572-6· OSTI ID:22943129

Sokolovskaya, M. V. ^[1]; Birin, K. P. ^[2]; Davankov, V. A. ^[1]

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1. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds (Russian Federation)
2. Russian Academy of Sciences, A. N. Frumkin Institute of Physical Chemistry and Electrochemistry (Russian Federation)

A novel chiral phosphoramidite ligand, (S{sub a})-2-[N-ethyl-N-(1-naphthylmethyl)amino]-dinaphtho[2,1-d:1´,2´-f][1,3,2]dioxaphosphepane, was obtained and tested in Ir-catalyzed asymmetric hydrogenation of a series of 4-R-1,3-dihydro-2H-1,5-benzodiazepin-2-ones, wherein up to 74% ee was achieved. The structure of the resulting compounds was determined based on one- and two-dimensional NMR ({sup 1}H, {sup 13}C, {sup 31}P, {sup 1}H—{sup 1}H COSY, {sup 1}H—{sup 1}H ROESY, {sup 1}H—{sup 13}C HSQC and {sup 1}H—{sup 13}C HMBC) spectroscopy data.

• OSTI ID: 22943129
• Journal Information: Russian Chemical Bulletin, Vol. 68, Issue 7; Other Information: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature; Article Copyright (c) 2019 Springer Science+Business Media, Inc.; Country of input: International Atomic Energy Agency (IAEA); ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ASYMMETRY
CARBON 13
CHIRALITY
COSY STORAGE RING
HYDROGEN 1
HYDROGENATION
LIGANDS
NUCLEAR MAGNETIC RESONANCE
PHOSPHORUS 31
SPECTROSCOPY
TWO-DIMENSIONAL CALCULATIONS
TWO-DIMENSIONAL SYSTEMS