798827

(S)-N-Butyl-1-[(2-hydroxybenzyl)-L-valyl]pyrrolidine-2-carboxamide

• Synonym(s): Yoon Syn-[2+2]-Photocycloaddition Ligand
• Empirical Formula (Hill Notation): C₂₁H₃₃N₃O₃
• CAS Number: 1613249-60-7
• Molecular Weight: 375.51
• UNSPSC Code: 12352111
• PubChem Substance ID: 329768672
• NACRES: NA.22

Properties

• form: liquid
• storage temp.: 2-8°C
• SMILES string: OC1=C(CN[C@@H](C(C)C)C(N2[C@H](C(NCCCC)=O)CCC2)=O)C=CC=C1
• InChI: 1S/C21H33N3O3/c1-4-5-12-22-20(26)17-10-8-13-24(17)21(27)19(15(2)3)23-14-16-9-6-7-11-18(16)25/h6-7,9,11,15,17,19,23,25H,4-5,8,10,12-14H2,1-3H3,(H,22,26)/t17-,19-/m0/s1
• InChI key: YETNAJXRRQTUPV-HKUYNNGSSA-N

Description

General description

(S)-N-Butyl-1-[(2-hydroxybenzyl)-L-valyl]pyrrolidine-2-carboxamide is a secondary amine ligand. It act as a Lewis acid co-catalyst for [2+2] cycloaddition on complexation with Eu(OTf)₃ (europium(III)triflate).[1]

Application

Chiral ligand for the asymmetric [2+2] cycloaddition of enones by photoredox catalysis.

Other Notes

A Dual-Catalysis Approach to Enantioselective [2 + 2] Photocycloadditions Using Visible Light

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable