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683981

Sigma-Aldrich

(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H, 6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate

97%

Synonym(s):

Bode Catalyst 1

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About This Item

Empirical Formula (Hill Notation):
C21H22ClN3O · H2O
Molecular Weight:
385.89
UNSPSC Code:
12352005
PubChem Substance ID:
329760887

Assay

97%

form

solid

optical activity

[α]20/D -156.0°, c = 1 in chloroform

mp

212-216 °C

SMILES string

[Cl-].Cc1cc(C)c(c(C)c1)-[n+]2c[n@H]3[C@H]4[C@H](Cc5ccccc45)OCc3n2

InChI

1S/C21H22N3O.ClH/c1-13-8-14(2)20(15(3)9-13)24-12-23-19(22-24)11-25-18-10-16-6-4-5-7-17(16)21(18)23;/h4-9,12,18,21H,10-11H2,1-3H3;1H/q+1;/p-1/t18-,21+;/m0./s1

InChI key

GUECWMLEUCWYOS-OZYANKIXSA-M

Application

(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H, 6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate can be used as an N-heterocyclic carbene (NHC) organocatalyst:
  • In the synthesis of tricyclic β-lactones by reacting 2-bromoenals with 1,3-diketones.
  • To functionalize the C2-position of 3-aminobenzofurans using 2-bromoenals as coupling partners.
  • In the synthesis of dihydroquinoxalines from substituted bisimines.
  • In the preparation of spiro-glutarimide derivatives by reacting cyclic β-ketoamides with α,β-unsaturated aldehydes.

Legal Information

Sold in collaboration with BioBlocks, Inc.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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N-heterocyclic carbene-catalyzed enantioselective synthesis of spiro-glutarimides via α, β-unsaturated acylazoliums
Mondal S, et al.
Organic Letters, 20(15), 4499-4503 (2018)
Catalytic, Enantioselective C2-Functionalization of 3-Aminobenzofurans Using N-Heterocyclic Carbenes
Barik S, et al.
Organic Letters, 22(10), 3865?3869-3865?3869 (2020)
Enantioselective Synthesis of Tricyclic β-Lactones by NHC-Catalyzed Desymmetrization of Cyclic 1, 3-Diketones
Shee S, et al.
Organic Letters, 22(14), 5407?5411-5407?5411 (2020)
N-Heterocyclic Carbene-Catalyzed Umpolung of Imines for the Enantioselective Synthesis of Dihydroquinoxalines
Das TK, et al.
ACS Catalysis, 9(5), 4065-4071 (2019)

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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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