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Merck
CN

798827

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

Synonym(s):

Yoon Syn-[2+2]-Photocycloaddition Ligand

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About This Item

Empirical Formula (Hill Notation):
C21H33N3O3
CAS Number:
1613249-60-7
Molecular Weight:
375.51
UNSPSC Code:
12352111
PubChem Substance ID:
329768672
NACRES:
NA.22

Key Documents

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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

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).

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Juana Du et al.
Science (New York, N.Y.), 344(6182), 392-396 (2014-04-26)
In contrast to the wealth of catalytic systems that are available to control the stereochemistry of thermally promoted cycloadditions, few similarly effective methods exist for the stereocontrol of photochemical cycloadditions. A major unsolved challenge in the design of enantioselective catalytic

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