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Published TCIMAIL newest issue No.198

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CAS RN: 1223020-29-8 | Product Number: B3934

2,6-Bis[(2R,4S,5S)-1-benzyl-4,5-diphenylimidazolidin-2-yl]pyridine

Purity: >90.0%(HPLC)

Synonyms:

PyBidine

Product Documents:

Size	Unit Price	Belgium	Japan*	Quantity
50MG	€87.00	2	≥100

*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).

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General Information plus

Product Number	B3934
Purity / Analysis Method	>90.0%(HPLC)
Molecular Formula / Molecular Weight	C₄₉H₄₅N₅ = 703.93
Physical State (20 deg.C)	Solid
Storage Temperature	Frozen (<0°C)
Condition to Avoid	Heat Sensitive
CAS RN	1223020-29-8
Reaxys Registry Number	20348189
PubChem Substance ID	160871049

Specifications & Properties plus

Safety & Regulations plus

Applications & Literature plus

Application

Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using PyBidine-Metal Catalysts

B3934

Typical Procedure (Cat.: Ni(OAc)₂ ·4H₂O, Ar: Ph): PyBidine (15.5 mg, 0.022 mmol) and Ni(OAc)₂ ·4H₂O (12.3 mg, 0.02 mmol) are added to a flask under Ar. Dichloromethane (1.00 mL) is added to the flask and the mixture is stirred for 3 hours. After removal of the solvent under reduced pressure, dioxane (1.00 mL) is added as a reaction solvent. To the resulting solution, nitromethane (122 mg, 2.00 mmol), DIPEA (2.6 mg, 0.02 mmol) and tert-butyl benzylidenecarbamate (41.1 mg, 0.20 mmol) are added at r.t. After being stirred for 24 hours, the reaction mixture is quenched by saturated NaHCO₃ aq., extracted with dichloromethane, and dried over Na₂SO₄. After removal of the solvent under reduced pressure, the resulting crude mixture is purified by silica gel column chromatography to give (R)-tert-butyl 2-nitro-1-phenylethylcarbamate (90% yield, 89% ee).

References

T. Arai, E. Matsumura, Synlett 2014, 25, 1776.

Application

Useful Asymmetric Organoligands for [3+2] Cycloaddition

References

1)Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism: diamine?Cu^I-catalyzed asymmetric Henry reaction
- T. Arai, M. Watanabe, A. Fujiwara, N. Yokoyama, A. Yanagisawa, Angew. Chem. Int. Ed. 2006, 45, 5978.
2)A library of chiral imidazoline?aminophenol ligands: discovery of an efficient reaction sphere
- T. Arai, N. Yokoyama, A. Yanagisawa, Chem. Eur. J. 2008, 14, 2052.
3)Chiral bis(imidazolidine)pyridine?Cu(OTf)₂: catalytic asymmetric endo-selective [3+2] cycloaddition of imino esters with nitroalkenes
- T. Arai, A. Mishiro, N. Yokoyama, K. Suzuki, H. Sato, J. Am. Chem. Soc. 2010, 132, 5338.
4)syn-Selective asymmetric Mannich reaction of sulfonyl imines with iminoesters catalyzed by the N,N,N-tridentate bis(imidazolidine)pyridine (PyBidine)?Cu(OTf)₂ complex
- T. Arai, A. Mishiro, E. Matsumura, A. Awata, M. Shirasugi, Chem. Eur. J. 2012, 18, 11219.
5)Catalytic asymmetric exo’ -selective [3+2] cycloaddition of iminoesters with nitroalkenes
- T. Arai, N. Yokoyama, A. Mishiro, H. Sato, Angew. Chem. Int. Ed. 2010, 49, 7895.

PubMed Literature

Articles/Brochures

Useful Chiral Ligands for Asymmetric [3+2] Cycloaddition

Chiral Ligands

Ligands

TCIMAIL

[TCIMAIL No.156] Useful Asymmetric Organoligands for [3+2] Cycloaddition
[Research Articles] Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using PyBidine-Metal Catalysts

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Product Categories

Chemistry

Catalysis and Inorganic Chemistry

Nitrogen-Donor Ligands [Catalysis]

Pyridine Ligands

Chemistry

Catalysis and Inorganic Chemistry

Nitrogen-Donor Ligands [Catalysis]

Pyridine Ligands

Appearance	White to Light yellow powder to crystal
Purity(HPLC)	min. 90.0 area%
Specific rotation [a]20/D	-98.0 to -100.0 deg(C=1, CHCl3)
NMR	confirm to structure

Pictogram
Signal Word	Warning
Hazard Statements	H315 : Causes skin irritation. H319 : Causes serious eye irritation.
Precautionary Statements	P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention.

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CAS RN: 1223020-29-8 | Product Number: B3934

2,6-Bis[(2R,4S,5S)-1-benzyl-4,5-diphenylimidazolidin-2-yl]pyridine

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References

Articles/Brochures

Safety Data Sheet (SDS)

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C of A & Other Certificates

Sample C of A

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Chemistry

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CAS RN: 1223020-29-8 | Product Number: B3934

2,6-Bis[(2R,4S,5S)-1-benzyl-4,5-diphenylimidazolidin-2-yl]pyridine

References

References

Articles/Brochures

Safety Data Sheet (SDS)

Specifications

C of A & Other Certificates

Sample C of A

Analytical Charts

Other Documents

Product Categories

Chemistry

Chemistry