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Synthesis and applications of a highly fluorous alkoxy ethyl ether protective group

✍ Scribed by Peter Wipf; Jonathan T. Reeves

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
278 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A readily recyclable, fluorous alkoxy ethyl ether protecting group has been developed that allows for simple purification of small to medium-sized organic molecules by liquid-liquid extraction with FC-72/organic/aqueous solvents. The precursor vinyl ether 3 can be prepared in large quantity in a straightforward two step reaction sequence. Primary, secondary, and tertiary alcohols are protected in good to excellent yields, and the fluorous label is removed by mild acid treatment. The N-protection of 2-fluoroaniline demonstrates the feasibility of using 3 with amines.

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Synthesis and Applications of a Fluorous THP Protective Group. -A variety of alcohols (IX) can be protected with a fluorous labeled THP protecting group using the Cp 2 ZrCl 2 -AgClO 4 reagent system to activate the sulfoxide (VII). The protected alcohols (X) can be easily purified by liquid-liquid