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Merck
CN

683558

(S)-Mac-H

Synonym(s):

MacMillan catalyst - Hantzsch Ester combination

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About This Item

Linear Formula:
(C13H19NO4)6 (C8H16N2O · CF3CO2H)1
NACRES:
NA.22
PubChem Substance ID:
329760823
UNSPSC Code:
12352005
MDL number:
MFCD09750462

Key Documents

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InChI

1S/6C13H19NO4.C8H16N2O.C2HF3O2/c6*1-5-17-12(15)10-7-11(13(16)18-6-2)9(4)14-8(10)3;1-8(2,3)7-9-5-6(11)10(7)4;3-2(4,5)1(6)7/h6*14H,5-7H2,1-4H3;7,9H,5H2,1-4H3;(H,6,7)/t;;;;;;7-;/m......0./s1

SMILES string

OC(=O)C(F)(F)F.CN1[C@H](NCC1=O)C(C)(C)C.CCOC(=O)C2=C(C)NC(C)=C(C2)C(=O)OCC.CCOC(=O)C3=C(C)NC(C)=C(C3)C(=O)OCC.CCOC(=O)C4=C(C)NC(C)=C(C4)C(=O)OCC.CCOC(=O)C5=C(C)NC(C)=C(C5)C(=O)OCC.CCOC(=O)C6=C(C)NC(C)=C(C6)C(=O)OCC.CCOC(=O)C7=C(C)NC(C)=C(C7)C(=O)OCC

InChI key

NWCRTIKSGFXFGW-KDCVMDMUSA-N

form

solid

Application

A mixture of a chiral imidazolidinone with the Hantzsch ethyl ester; formally transfers hydrogen asymmetrically to enals resulting in chiral aldehydes.

Legal Information

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBB8310V
MKBB8310
09409BH

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Stéphane G Ouellet et al.
Journal of the American Chemical Society, 127(1), 32-33 (2005-01-06)
The first enantioselective organocatalytic hydride reduction has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of beta,beta-substituted alpha,beta-unsaturated aldehydes to generate beta-stereogenic aldehydes. The use of imidazolidinone 2 as the asymmetric

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