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
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C11H10BrNO3
CAS Number:
Molecular Weight:
284.11
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
form
solution
Quality Level
functional group
bromo, ether
storage temp.
15-25°C
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
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.
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Related Content
Bode Group creates N-mesityl-NHC catalysts for enantioselective annulations and SnAP reagents for one-pot aldehyde conversion into N-heterocycles.
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 804568-100MG | 04061833243732 |