395242
(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol
99%
About This Item
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Quality Level
assay
99%
form
solid
optical activity
[α]20/D +280°, c = 1 in ethyl acetate
mp
200 °C (dec.) (lit.)
SMILES string
CC1(C)O[C@@H]([C@H](O1)C(O)(c2cccc3ccccc23)c4cccc5ccccc45)C(O)(c6cccc7ccccc67)c8cccc9ccccc89
InChI
1S/C47H38O4/c1-45(2)50-43(46(48,39-27-11-19-31-15-3-7-23-35(31)39)40-28-12-20-32-16-4-8-24-36(32)40)44(51-45)47(49,41-29-13-21-33-17-5-9-25-37(33)41)42-30-14-22-34-18-6-10-26-38(34)42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1
InChI key
WTZVNZRNIOJACO-CXNSMIOJSA-N
Application
- For the highly enantioselective addition of primary alkyl Grignards to ketones.
- As an organocatalyst for the activation of carbonyl functionality in vinylogous addition reaction of an aldehyde.
- As a chiral dopant in the preparation of cholesteric liquid crystal (CLC) having an aggregation-induced-emission dye.
Certificates of Analysis (COA)
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Articles
The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as stoichiometric chiral reagents or in Lewis acid mediated reactions, to roles in catalytic hydrogenation and stereoregular metathesis polymerization.
Apart from numerous examples using TADDOLs in metal-catalyzed asymmetric reactions, Rawal recently reported that TADDOLs could be used as Brønsted acid organocatalysts in highly stereoselective hetero-Diels–Alder reactions.
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