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393762

Sigma-Aldrich

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)-1,3-dioxolane-4,5-dimethanol

98%

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Synonym(s):
(+)-2,3-O-Isopropylidene-1,1,4,4-tetra(2-naphthyl)-D-threitol, (+)-DINOL, (4S,5S)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)dioxolane-4,5-dimethanol
Empirical Formula (Hill Notation):
C47H38O4
CAS Number:
Molecular Weight:
666.80
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

98%

optical activity

[α]20/D +116°, c = 1 in ethyl acetate

optical purity

ee: 99% (HPLC)

mp

214-216 °C (lit.)

SMILES string

CC1(C)O[C@@H]([C@H](O1)C(O)(c2ccc3ccccc3c2)c4ccc5ccccc5c4)C(O)(c6ccc7ccccc7c6)c8ccc9ccccc9c8

InChI

1S/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1

InChI key

QWADMRIAKWGVBF-CXNSMIOJSA-N

Application

Reagent for the highly enantioselective addition of primary alkyl Grignards to ketones. Chiral auxiliary used for the asymmetric addition of nucleophiles to carbonyls.

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D. Seebach et al.
Angewandte Chemie (International Edition in English), 103, 991-991 (1991)
B. Schmidt et al.
Angewandte Chemie (International Edition in English), 103, 100-100 (1991)
Angewandte Chemie (International Edition in English), 31, 84-84 (1992)

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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