265004
(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol
97%
Synonym(s):
(−)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol, (−)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4R,5R)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane, 1,1,4,4-Tetraphenyl-2,3-O-isopropylidene-L-threitol, TADDOL
About This Item
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Quality Level
Assay
97%
optical activity
[α]19/D −62.6°, c = 1 in chloroform
mp
193-195 °C (lit.)
SMILES string
CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccccc2)c3ccccc3)C(O)(c4ccccc4)c5ccccc5
InChI
1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1
InChI key
OWVIRVJQDVCGQX-VSGBNLITSA-N
Application
Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides
Reactant or reagent involved in:
- Enantioswitching of catalytic asymmetric hydroboration
- Synthesis of derivative ligands for asymmetric hydroformylation of alkenes
- Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes
- Addition of deactivated alkyl Grignard reagents to aldehydes
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
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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.
Chiral Diols
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