Chromium vinylidene carbenoids: Stereospecific synthesis of (Z)-2-chloroalk-2-en-1-Ols

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4237-4238

  Barma, D K ^a   Baati, Rachid ^b   Valleix, Alain ^c   Mioskowski, Charles ^b   Falck, J R ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBENE; CHROMIUM; DRUG DERIVATIVE; HYDROCARBON; METHANE; VINYL DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; CHROMIUM; HYDROCARBONS; METHANE; VINYL COMPOUNDS;

EID: 0035961016     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016935h     Document Type: Article

References (16)

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2. 2-based methodology, see: (a) Falck, J. R.; Barma, D. K.; Baati, R.; Mioskowski, C. Angew. Chem., Int. Ed. 2001, 40, 1281-1283.
3. (b) Baati, R.; Valleix, A.; Mioskowski, C.; Barma, D. K.; Falck, J. R. Org. Lett. 2000, 2, 485-487.
4. Baati, R.; Barma, D. K.; Falck, J. R.; Mioskowski, C. J. Am. Chem. Soc. 2001, 123, 9196-9197.
5. 2,2,2-Trichloroethanol derivatives also yield (Z)-2-chloroalk-2-en-1-ols accompanied by variable amounts of 1,1-dichloroalkene, (EIZ)-1-chloroalkene, and 1-alkoxy-1-chloroalkene: Takai, K.; Kokumai, R.; Nobunaka, T. Chem. Commun. 2001, 1128-1129.
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13. 2 (1.6 mmol) in THF (10 mL) under argon at ambient temperature. After 10-12 h, the resultant reddish reaction mixture was quenched with water and extracted thrice with ether, and the combined ethereal extracts were evaporated in vacuo. Chromatographic purification on SiO2 gave the (Z)-chloroalkenol adducts in the indicated yields (Table 1).
14. Additions to ketones were sluggish, even at 75-80 °C, and gave low yields (10-15%) of the chloroalkenol adducts under the standard reaction conditions.
15. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349-12357.
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