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804584

Sigma-Aldrich

(S,R)-Bode Kinetic Resolution Catalyst

Synonym(s):

(4aS,9aR)-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:
1417826-81-3
Molecular Weight:
284.11
UNSPSC Code:
12352101
PubChem Substance ID:
329768884
NACRES:
NA.22

form

solution

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+/m1/s1

InChI key

FQXSUQCCAHKURK-KOLCDFICSA-N

Application

The following organocatalyst is used in the kinetic resolution of cyclic amines as reported by Bode and coworkers. In tandem with acylating reagent, (1E)-4-Hydroxy-1-mesityl-4-methylpent-1-en-3-one, either enantiomer can be accessed by using the catalyst shown or its enantiomer, both of which are available from Sigma-Aldrich.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Related Content

Bode Group – Professor Product Portal

The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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