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677183

Sigma-Aldrich

(S)-(–)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether

95%

Synonym(s):

(2S)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine, (S)-α,α-Diphenylprolinol trimethylsilyl ether, (S)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine

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About This Item

Empirical Formula (Hill Notation):
C20H27NOSi
CAS Number:
848821-58-9
Molecular Weight:
325.52
MDL number:
MFCD08690083
UNSPSC Code:
12352005
PubChem Substance ID:
24885354
NACRES:
NA.22

Assay

95%

optical activity

[α]22/D -50°, c = 1 in chloroform

refractive index

n20/D 1.5513

density

1.0459 g/mL at 25 °C

functional group

phenyl

storage temp.

2-8°C

SMILES string

C[Si](C)(C)OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3

InChI

1S/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m0/s1

InChI key

RSUHWMSTWSSNOW-IBGZPJMESA-N

Application

Organocatalyst for 3-component reactions, and Robinson annulation of α,β-unsaturated aldehydes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF1154V
WXBF2139V
WXBD8444V
WXBD7073V
WXBD2063V

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Bor-Cherng Hong et al.
The Journal of organic chemistry, 72(22), 8459-8471 (2007-10-09)
The highly enantioselective organocatalytic Robinson annulation of alpha,beta-unsaturated aldehydes was achieved, catalyzed by l-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the
Dieter Enders et al.
Nature, 441(7095), 861-863 (2006-06-17)
Efficient and elegant syntheses of complex organic molecules with multiple stereogenic centres continue to be important in both academic and industrial laboratories. In particular, catalytic asymmetric multi-component 'domino' reactions, used during total syntheses of natural products and synthetic building blocks
Chemical and Engineering News, June (2006)

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