Highly diastereoselective titanium(II)-mediated cyclizations of 1,7-(silyloxy)enynes

Arkivoc

Volumn 2008, Issue 16, 2008, Pages 110-118

  Barbour, Nicole M ^a   Phillips, Andrew J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

Cyclic siloxanes; Cyclization; Enyne; Low valent titanium; Silicon tethered reactions

Indexed keywords

EID: 77958046395     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.g11     Document Type: Article

References (5)

1. O'Neil, G. W.; Phillips, A. J. Tetrahedron Lett. 2004, 45, 4253
2. O'Neil, G. W.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 5340.
3. Keaton, K. A.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 408
4. Readily prepared by Barbier-type allylation using allyl bromide and zinc. See Hoffman, R.; Brueckner, R.; Chem. Ber. 1992, 125, 2731.
5. Ozonolysis of this alkene and reduction of the aldehyde provided a diol for which data could be compared to the known 2,4-anti-2,5-dimethylhexane-1,4- diol. See: Still, W. C.; Darst, K. P. J. Am. Chem. Soc. 1980, 102, 7385.