3-Isopropyl-2-cyclopenten-1-one → (s)-3-Isopropylcyclopentanone

HRID 1006189

Reaktionsgleichung

Reaktionsgleichung von HRID 1006189
CC1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.[CH:51]([C:54]1[CH2:58][CH2:57][C:56](=[O:59])[CH:55]=1)([CH3:53])[CH3:52]>>[CH:51]([C@H:54]1[CH2:58][CH2:57][C:56](=[O:59])[CH2:55]1)([CH3:53])[CH3:52]

Komponenten

3

Edukt 2

HCID 5575993-Isopropyl-2-cyclopenten-1-oneHCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthyl

Produkt 1

HCID 10855459(s)-3-IsopropylcyclopentanoneAusbeute 89 %

Versuchsvorschrift

General procedure B using (S)-p-tol-BINAP and 3-isopropylcyclopentenone (0.11 g, 0.9 mmol) gave, after 3 d at 0° C. and Kugelrohr distillation (0.4 torr, 220° C.) followed by flash chromatography (10:1 pentane:diethyl ether), the title compound as a clear liquid (0.10 g, 89% yield). In addition to the desired product, starting material (0.011 g, 10%) was also isolated. Spectroscopic data for the title compound were consistent with previously reported data.16 [α]D25° C.−200° (c 1.6, CHCl3) (lit.16 [α]D25° C.−110° (c 1.0, CHCl3) for 60% ee). Chiral GC analysis (Chiraldex G-TA column) indicated that the title compound was obtained in 95% ee.

Aufarbeitung

  1. customgave, after 3 d at 0° C.
  2. distillationKugelrohr distillation (0.4 torr, 220° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f0348b31ac4940c3a96ce13ccb7ff005
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787655B2

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