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Sigma-Aldrich

(R,S)-Bode Kinetic Resolution Catalyst

Synonym(e):

(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

Empirische Formel (Hill-System):
C11H10BrNO3
CAS-Nummer:
1394957-71-1
Molekulargewicht:
284.11
UNSPSC-Code:
12352101
PubChem Substanz-ID:
329768882
NACRES:
NA.22

Form

solution

Qualitätsniveau

100

Lagertemp.

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

InChIKey

FQXSUQCCAHKURK-GXSJLCMTSA-N

Anwendung

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.

Sonstige Hinweise

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

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)

Verwandter Inhalt

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.

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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