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669490

Sigma-Aldrich

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

95%

Synonym(s):

(1R,4R,8R) Carreira DOLEFIN Ligand, (1R,4R,8R)-8-Methoxy-1,8-dimethyl-2-(2-methylpropyl)-5-(phenylmethyl)bicyclo[2.2.2]octa-2,5-diene

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About This Item

Empirical Formula (Hill Notation):
C22H30O
CAS Number:
948594-95-4
Molecular Weight:
310.47
MDL number:
MFCD08702680
UNSPSC Code:
12352112
PubChem Substance ID:
24885054

Assay

95%

form

liquid

optical activity

[α]20/D +98±5°, c = 0.7 in chloroform

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.5205

functional group

ether
phenyl

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-/m1/s1

InChI key

ACWLDJOHMGJACE-BHIFYINESA-N

Application

Carreira DOLEFIN Ligands
(1R, 4R, 8R) Carreira DOLEFIN Ligand is a chiral diene ligand that can be used in:
  • The asymmetric Rh-catalyzed arylation of alkenylheterocycles by conjugate additions with various aryl boronic acids.
  • The enantioselective synthesis of 3,3-diarylpropanals by conjugate addition of aromatic boronic acids to cinnamaldehyde derivatives in the presence of a rhodium catalyst.
  • The asymmetric synthesis of pyrrolizidinones by rhodium-catalyzed 1,4-addition of aryl boronic acids to pyrrolidine acceptor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC2213
MKBV8557V
MKBN3483V
MKBF0760V
MKBD5021

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Rhodium-catalyzed 1, 4-additions to enantiopure acceptors: Asymmetric synthesis of functionalized pyrrolizidinones
Zoute L, et al.
Organic Letters, 11(12), 2491-2494 (2009)
Asymmetric Synthesis of 3, 3-Diarylpropanals with Chiral Diene- Rhodium Catalysts
Paquin J-F, et al.
Journal of the American Chemical Society, 127(31), 10850-10851 (2005)
Enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylheteroarenes
Pattison G, et al.
Journal of the American Chemical Society, 132(41), 14373-14375 (2010)
Jean-François Paquin et al.
Journal of the American Chemical Society, 127(31), 10850-10851 (2005-08-04)
A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as
Jean-François Paquin et al.
Organic letters, 7(17), 3821-3824 (2005-08-12)
A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both

Articles

Carreira DOLEFIN Ligands

The selective preparation of diarylmethine stereogenic centers is a challenging endeavor in chemical synthesis, especially when there is little differentiation between the two aryl groups

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