References

Main Paper Citation:

Arnold, M. A.; Day, K. A.; Durón, S. G.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 13255–13260.

 

Section Citation:

Wang, Q.; Wei, H.-X.; Schlosser, M. Eur. J. Org. Chem. 1999, 13, 3263-3268.

 

In this article, hemiacetals and hemiaminals undergo a stereoselective Wittig reaction with simultaneously generated phosphorus ylides to produce olefins in very high overall yields.

 

Other Citations:

Konev, A. S.; Khlebnikov, A. F. Collection of Czechoslovak Chemical Communications 2008, 73, 1553-1611.

 

In this article, the phosphorous ylide was prepared by reacting CFBr3 with Ph3P, which reacts with aldehydes and ketones. A Wittig reaction was then performed in order to yield gem-bromofluoroalkenes.

 

van Steenis, J. H.; van der Gen, A. European Journal of Organic Chemistry 2001, 5, 897-910.

 

In this article, the authors talked about the classic Wittig reaction with (fluoromethyl)di-phenylphosphonium salts, noting how these only gave moderate yields and lacked stereoselectivity. After, it refers to this citation, noting that the simultaneous generation of the ylide and benzaldehyde did give high yields.

 

Risi, R. M.; Maza, A. M.; Burke, S. D. J. Org. Chem. 2015, 80, 204-216.

 

(+)-patulolide C was synthesized, as well as three specific stereoselecctive products. An AHF/intramolecular Wittig olefination cascade was used to set the C4-hydroxyl stereochemistry, E- olefin geometry, and form the macrolactone. Much of the focus of this article is on the stereoselectivity.