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Sigma-Aldrich

(R,S)-Bode Kinetic Resolution Catalyst

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Synonym(s):
(4aR,9aS)-6-Bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one
Empirical Formula (Hill Notation):
C11H10BrNO3
CAS Number:
Molecular Weight:
284.11
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

form

solution

Quality Level

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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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)

Related Content

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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