Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide

Organic Letters

Volumn 3, Issue 6, 2001, Pages 937-939

  Concellön, José M ^a   Bernad, Pablo L ^a   Bardales, Eva ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

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EID: 0000363311     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015601p     Document Type: Article

References (29)

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2. For a review, see: (a) Colvin, E. W. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 2, pp 5-8; Vol. 11, pp 315-317.
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21. 1H NMR and GC/MS to give the diastereoisomeric excess reported in Table 2. Distillation at reduced pressure provided pure (Z)-vinylsilanes 3.
22. 4Cl (25 mL), and after usual workup, the corresponding crude 1-chloro-1-trimethylsilylalkan-2-ol was obtained. This alcohol (8 mmol) was treated with pyridine (25 mL), acetic anhydride, and 4-(dimethylamino)-pyridine (5 mg). After being stirred for 12 h, the mixture was treated with ice, and after usual workup, the corresponding crude O-acetyl 1-chloro-1-trimethylsilylalkan-2-ol 1 was obtained. The crude products 1 were used without further purification.
23. Günter, H. NMR spectroscopy; Wiley: England, 1996; p 119.
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