804568
(R,S)-Bode Kinetic Resolution Catalyst
别名:
(4aR,9aS)-6-Bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one
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关于此项目
经验公式（希尔记法）:
C11H10BrNO3
化学文摘社编号:
分子量:
284.11
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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
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
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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)
相关内容
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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