Selective one-pot synthesis of Z-iodoallylic iodides from propargyl alcohols

Tetrahedron Letters

Volumn 47, Issue 33, 2006, Pages 5867-5868

  Manickam, Govindaswamy ^a   Siddappa, Umesh ^a   Li, Yong ^b  

^a SYNGENE INTERNATIONAL LTD   (India)

^b KOSAN BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; IODINE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; SYNTHESIS;

EID: 33745761498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.081     Document Type: Article

References (5)

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2. Kagechika K., Ohshima T., and Shibasaki M. Tetrahedron 49 (1993) 1773
3. Sato Y., Nukui S., Sodeoka M., Mikiko S., and Shibasaki M. Tetrahedron 50 (1994) 371
4. Gras J.-L., Chang K.W., and Bertrand M. Tetrahedron Lett. 23 (1982) 3571
5. Trimethylsilyl iodide was purchased from Lancaster Chemical Co. and was used directly. Zinc chloride was purchased from Aldrich Chemical Co. and fused prior to use. Experimental procedure: To a solution of 2-butyn-1-ol (45 g, 0.64 mol) in dry dichloromethane (500 mL) was added freshly fused zinc chloride (13 g, 0.096 mol) under nitrogen atmosphere. The reaction mixture was cooled to -40 °C, and trimethylsilyl iodide was then introduced slowly under dark over a period of 30 min. The reaction mixture was slowly warmed to 0 °C and stirred for 1 h. It was filtered over a bed of celite and concentrated. The crude residue was subjected to vacuum distillation to give diiodide 1 as a brown oil (bp 59-62 °C/0.1 mm Hg, 184 g, 93%).