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685429

Sigma-Aldrich

(R)-Mac-H

Synonym(s):

MacMillan catalyst - Hantzsch Ester combination

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About This Item

Linear Formula:
(C13H19NO4)6 (C8H16N2O · CF3CO2H)1
UNSPSC Code:
12352005
PubChem Substance ID:
24885839

form

solid

mp

99-145 °C

functional group

carboxylic acid
ester
fluoro

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

InChI

1S/C13H19NO4.C8H16N2O.C2HF3O2/c1-5-17-12(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/h14H,5-7H2,1-4H3;7,9H,5H2,1-4H3;(H,6,7)/t;7-;/m.1./s1

InChI key

VPEIUDRYFWHOML-QABCSGHHSA-N

Application

A mixture of a chiral imidazolidinone with the Hantzsch ethyl ester; formally transfers hydrogen asymmetrically to enals resulting in chiral aldehydes.[1]

Legal Information

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBD2443V
MKBD2443
05409DH

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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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