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804568

Sigma-Aldrich

(R,S)-Bode Kinetic Resolution Catalyst

Synonyme(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

Formule empirique (notation de Hill):
C11H10BrNO3
Numéro CAS:
1394957-71-1
Poids moléculaire :
284.11
Code UNSPSC :
12352101
ID de substance PubChem :
329768882
Nomenclature NACRES :
NA.22

Forme

solution

Niveau de qualité

100

Température de stockage

15-25°C

Chaîne SMILES 

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

Clé InChI

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.

Autres remarques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Conseils de prudence

P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)

Contenu apparenté

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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