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449539

Sigma-Aldrich

Chlorocyclopentadienyl[(4S,5S)-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium

97%

Synonym(s):

(4S,5S)-Chloro-cyclopentadienyl-[2,2-dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]titanium, (S,S)-Duthaler-Hafner reagent, [(4S,5S)-2,2-Dimethyl-1,3-dioxolan-4,5-bis(diphenylmethoxy)]cyclopentadienyl-chlorotitanium

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About This Item

Empirical Formula (Hill Notation):
C36H33ClO4Ti
CAS Number:
140462-73-3
Molecular Weight:
612.96
UNSPSC Code:
12352000
PubChem Substance ID:
24868490

assay

97%

optical activity

[α]20/D +246°, c = 1 in chloroform

mp

209-213 °C (lit.)

SMILES string

Cl[Ti].[CH]1[CH][CH][CH][CH]1.CC2(C)O[C@@H]([C@H](O2)C(O)(c3ccccc3)c4ccccc4)C(O)(c5ccccc5)c6ccccc6

Application

A novel highly enantioselective allyl-transfer reagent. Excellent regio-, diastereo-, and enantioselectivities (usually >95% ee, >95% de) are obtained for the addition of allyl nucleophiles to aldehydes. Although this reagent is used in stoichiometric amounts, the chiral ligand and monocyclopentadienyltitanium trichloride can be easily recovered.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
318443/1
08422LN

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Duthaler, R.O. et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 62, 631-631 (1990)
Duthaler, R.O. et al.
Inorgorganica Chimica Acta, 222, 95-95 (1994)
Duthaler, R.O. et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 64, 1897-1897 (1990)
Duthaler, R.O. Hafner, A.
Chemical Reviews, 92, 807-807 (1992)
A. Hafner et al.
Journal of the American Chemical Society, 114, 2321-2321 (1992)

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