1-(Tert-butoxy)-4-ethenylbenzene → (1R,2R)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester

HRID 471431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471431
[C:1]([O:5][C:6]1[CH:13]=[CH:12]C(C=C)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]([C:26]1[O:27][CH2:28][C@H:29]([C:31]([CH3:34])([CH3:33])C)N=1)(C1OC[C@H](C(C)(C)C)N=1)(C)C.CCCCCC.C([OH:43])C>>[CH2:26]([O:27][C:28]([C@@H:29]1[CH2:34][C@H:31]1[C:33]1[CH:12]=[CH:13][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:7][CH:8]=1)=[O:43])[CH3:14]

Komponenten

4

Edukt 3

HCID 5775311-(Tert-butoxy)-4-ethenylbenzeneHCID 688208t-Bu-box, (S,S)-HCID 21879635Ethanol hexane

Produkt 1

HCID 72700305(1R,2R)-2-(4-tert-Butoxy-phenyl)-cyclopropanecarboxylic acid ethyl ester

Versuchsvorschrift

The title compound is prepared from 4-tert-butoxystyrene (4.3 g, 24.4 mmol) in a manner analogous to that described for Intermediate 4, step 1, using (S,S)-2,2′-isopropylidenebis(4-tert-butyl-2-oxazoline) (72 mg, 0.24 mmol) as the ligand (yield 6.4 g). LC (GC METHOD 1): tR=11.47 min; Mass spectrum (EI+): m/z=262 [M]+, e.e. 94% by chiral HPLC. (Column: Daicel Chiralcel OJ-H, 4.6×250 mm, 5 μm Mobile phase: hexane:ethanol 95:5, 1 mL/min, 25° C.) tR=8.94 (9.93) min

Quellen und Nachweise

ORD-Eintrag
ord-d1834ec71d474b1593c7a7f4dd7fe21d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633182B2

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