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2,2′-Isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline]

99%

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Synonym(s):
(S,S)-2,2′-Isopropylidene-bis(4-tert-butyl-2-oxazoline)
Empirical Formula (Hill Notation):
C17H30N2O2
CAS Number:
Molecular Weight:
294.43
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

99%

optical activity

[α]20/D −120°, c = 5 in chloroform

mp

89-91 °C (lit.)

SMILES string

CC(C)(C)[C@H]1COC(=N1)C(C)(C)C2=N[C@H](CO2)C(C)(C)C

InChI

1S/C17H30N2O2/c1-15(2,3)11-9-20-13(18-11)17(7,8)14-19-12(10-21-14)16(4,5)6/h11-12H,9-10H2,1-8H3/t11-,12-/m1/s1

InChI key

DPMGLJUMNRDNMX-VXGBXAGGSA-N

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405965407151405973
optical activity

[α]20/D −120°, c = 5 in chloroform

optical activity

[α]20/D −118°, c = 0.5 in chloroform

optical activity

[α]25/D −118°, c = 0.7 in methylene chloride

optical activity

[α]20/D −40.6°, c = 1 in ethanol

mp

89-91 °C (lit.)

mp

51-53 °C (lit.)

mp

155-157 °C (lit.)

mp

129-132 °C (lit.)

Application

Chiral catalyst for asymmetric synthesis. C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

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Description
Pricing

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Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Tetrahedron Letters, 45, 4213-4216 (2004)
Mauro Marigo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(9), 2133-2137 (2004-04-28)
The first general catalytic asymmetric bromination and chlorination of beta-ketoesters has been developed. The reactions proceed for both acyclic and cyclic beta-ketoesters catalyzed by chiral bisoxazolinecopper(II) complexes giving the corresponding optically active alpha-bromo- and alpha-chloro-beta-ketoesters in high yields and moderate
Nicholas Gathergood et al.
Organic & biomolecular chemistry, 2(7), 1077-1085 (2004-03-23)
The direct aldol reaction of 2-ketoesters catalyzed by chiral bisoxazoline copper(II) complexes has been investigated. First the direct homo-aldol reaction of ethyl pyruvate is reported which proceeds to give diethyl 2-hydroxy-2-methyl-4-oxoglutarate. This was isolated as the more stable optically active
Tetrahedron Letters, 44, 7849-7850 (2003)
L C Madoff et al.
Infection and immunity, 60(12), 4989-4994 (1992-12-01)
Group B streptococci (GBS) cause the majority of cases of neonatal sepsis and meningitis in the United States. Immunization of women of childbearing age is one strategy under consideration for the prevention of neonatal disease. The beta C protein, a

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