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709492

Sigma-Aldrich

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene

97%

Synonym(s):

(1S,4S,8S) Carreira DOLEFIN Ligand, (1S,4S,8S)--5-Benzyl-8-methoxy-1,8-dimethyl-2-(2′-methylpropyl)-bicyclo[2.2.2]octa-2,5-diene, (1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethyl-2-bicyclo[2.2.2]octa-2,5-diene

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About This Item

Empirical Formula (Hill Notation):
C22H30O
CAS Number:
Molecular Weight:
310.47
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.06

Quality Level

assay

97%

form

liquid

optical activity

[α]/D −84±5°, c = 0.5 in chloroform

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.522

SMILES string

CO[C@@]1(C)C[C@@]2(C)C=C(Cc3ccccc3)[C@@H]1C=C2CC(C)C

InChI

1S/C22H30O/c1-16(2)11-19-13-20-18(12-17-9-7-6-8-10-17)14-21(19,3)15-22(20,4)23-5/h6-10,13-14,16,20H,11-12,15H2,1-5H3/t20-,21+,22-/m0/s1

InChI key

ACWLDJOHMGJACE-BDTNDASRSA-N

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General description

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene, an enantiopure diene ligand developed by Carreira, is most commonly used in asymmetric catalysis. It is generally prepared from commercially available (R)-carvone.

Application

(1S,4S,8S)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene is mainly useful for the stereoselective synthesis of diarylmethine stereogenic centers.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to alpha, beta-unsaturated sulfones
Mauleon P and Carretero JC
Organic Letters, 6(18), 3195-3198 (2004)

Related Content

The Carreira Research Group is focused on expanding and creating access to uncharted landscape in chemical space. In joint efforts with SpiroChem, Carreira develops innovative spirocyclic building blocks, seeking to make them available to the community at large. Molecules constructed from these building blocks take on unique three-dimensional profiles due to the underlying spirocyclic scaffold, enriched by the presence of diverse combinations of exit vectors as sites for functionalization. Importantly, the spirocyclic building blocks possess physicochemical properties useful in the drug discovery process. Thus, drug leads can be tuned through appending these subunits to the periphery of a given scaffold. Moreover, these compact modules represent a useful collection of unprecedented inputs for fragment-based libraries. In all applications, the inherent novelty of the structure affords researchers new opportunities to run wild in their designs and avenues to chemical space – with their imagination as the sole limitations. We are proud to partner in the efforts to make these building blocks widely available.

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