Zr-Mediated hydroboration: Stereoselective synthesis of vinyl boronic esters

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8777-8780

  Wang, Yanong D ^a   Kimball, Gregory ^b   Prashad, Amar S ^a   Wang, Yan ^a  

^a WYETH RESEARCH   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKYNE; ESTER DERIVATIVE; OXYGEN; VINYL DERIVATIVE; ZIRCONIUM;

ARTICLE; HYDROBORATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 27744509928     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.031     Document Type: Article

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19. 20 and 4,4,5,5-tetramethyl-[1,3,2] dioxaborolane (958 mg, 7.49 mmol) was added bis(cyclopentadienyl)zirconium chloride hydride (183 mg, 0.714 mmol) and triethylamine (72 mg, 0.714 mmol). The resulting mixture was heated at 60°C for 16 h and diluted with hexanes. The precipitate was removed by filtering over a short pad of silica gel and washed with hexanes. The filtrate was concentrated and dried in vacuum to give 1.76 g (93% yield) of tert-butyl(dimethyl){[(5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxa- borolan-2-yl)hex-5-en-1-yl]oxy}silane as a colorless liquid.
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