Oxygen-directed intramolecular hydroboration

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9182-9183

  Rarig, Robert André F ^a   Scheideman, Matthew ^a   Vedejs, Edwin ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; BORANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; DIMETHYL SULFIDE; OXYGEN;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; HYDROBORATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY;

ALCOHOLS; ALKENES; BORANES; IODINE; OXIDATION-REDUCTION; PROPANOLS;

EID: 47749134240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800402g     Document Type: Article

References (22)

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15. 4COCl (resolved methine H's for all diol pairs except 9h/10h).
16. 2S during oxidative workup.
17. 1-Phenethyltetrahydrofuran was isolated in 6% yield using ODHB from 5i. Analogous (volatile) byproducts from TfOH-induced cyclization were detected in ODHB experiments with some of the other alcohols 5. The corresponding Li alkoxides give no cyclic ethers, but conversion was lower using 2 equiv of 3 (X = OTf) and the procedure more tedious.
18. 2 evolution thereafter (9% total after 1.5 h).
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21. 2S plays no major role.
22. 2 react with ≤1.5:1 dr.