Asymmetric aminohydroxylation of vinsylfuran

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2984-2985

  Bushey, Mark L ^a   Haukaas, Michael H ^a   O'Doherty, George A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE; UNCLASSIFIED DRUG; VINYLFURAN;

ARTICLE; CATALYSIS; CHROMATOGRAPHY; ENANTIOMER; HYDROXYLATION; METHODOLOGY; OXIDATION; SYNTHESIS;

EID: 0033617464     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990095r     Document Type: Article

References (32)

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17. This in situ use of vinylfuran allows for much higher yields of diol 6. Wittig technology provides vinylfuran in yields on the order of 10%. A previous approach to vinylfuran involves a four-step sequence from furfural that involves a stoichiometric Cu-mediated decarboxylation of 3-furylpropanoic acid, see: Schmidt, U.; Werner, J. Synthesis 1986, 986.
18. At a smaller scale, the level of enantioinduction has been as high as 94%, as determined by Mosher ester analysis.
19. This procedure was carried out with a slight excess of TBSCl compared to the primary alcohol and typically afforded less that 1% of the silyl-protected secondary alcohol.
20. This lower yield may be due to over-oxidation of the furan ring. We have observed that excess nitrene source or longer reaction times leads to furan oxidation.
21. These reactions were run to 70% conversion because of our concerns of oxidation of the furan ring (ref 18) and to prevent a ligandless background reaction.
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23. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045- 2048.
24. In addition to various electron rich styrene derivatives, excellent regioselectivity is observed in the aminohydroxylation of α,β-unsaturated esters. For cinnamates, see: (a) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507. (c) Also ref 9b. (d) For nonaromatic α,β-unsaturated esters, see: Han, H.; Yoon, J.; Janda, K. D. J. Org. Chem. 1998, 63, 2045- 2048.
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