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Merck
CN

804568

(R,S)-Bode Kinetic Resolution Catalyst

Synonym(s):

(4aR,9aS)-6-Bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one

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About This Item

Empirical Formula (Hill Notation):
C11H10BrNO3
CAS Number:
1394957-71-1
Molecular Weight:
284.11
MDL number:
MFCD29037020
UNSPSC Code:
12352101
PubChem Substance ID:
329768882
NACRES:
NA.22

Key Documents

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SMILES string

O=C(CO1)N(O)[C@@]2([H])[C@]1([H])CC3=CC=C(Br)C=C32

InChI

1S/C11H10BrNO3/c12-7-2-1-6-3-9-11(8(6)4-7)13(15)10(14)5-16-9/h1-2,4,9,11,15H,3,5H2/t9-,11+/m0/s1

InChI key

FQXSUQCCAHKURK-GXSJLCMTSA-N

form

solution

functional group

bromo, ether

storage temp.

15-25°C

Quality Level

100

Related Categories

Application

The following hydroxamic acid catalyst was shown by Bode and coworkers to assist in the kinetic resolution of cyclic amines through acylation of one enantiomer, which can be controlled using either the (R or S)- or (S or R)-Bode Kinetic Resolution Catalyst, both of which are also available through Sigma-Aldrich.
It can also be employed in the preparation of nonracemic piperidines by kinetic resolution using an α-hydroxy-α′, β-unsaturated ketone in the presence of a pyrrolotriazolium salt.

Other Notes

Expanded substrate scope and catalyst optimization for the catalytic kinetic resolution of N-heterocycles

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Concerted amidation of activated esters: Reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer
Allen SE, et al.
Journal of the American Chemical Society, 136(33), 11783-11791 (2014)
Catalytic kinetic resolution of disubstituted piperidines by enantioselective acylation: synthetic utility and mechanistic insights
Wanner B, et al.
Journal of the American Chemical Society, 137(35), 11491-11497 (2015)

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Bode Group – Prof. Product Portal

Bode Group creates N-mesityl-NHC catalysts for enantioselective annulations and SnAP reagents for one-pot aldehyde conversion into N-heterocycles.

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