A Short and Efficient Synthesis of l-5,5,5,5‘,5‘,5‘-hexafluoroleucine from N-Cbz-l-Serine
- 26 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (24) , 4281-4283
Abstract
5,5,5,5‘,5‘,5‘-Hexafluoroleucine (6), a fluorous analogue of leucine, is of considerable interest as a building block in the design of fluorous proteins and peptides. We report a short and efficient synthesis of 6, which is obtained from N-Cbz-l-serine (1) in 50% overall yield, 99% enantiomeric excess, and in multigram quantities. Key steps are addition of a serine-derived organozincate to hexafluoroacetone to construct the hexafluoroleucine side chain, followed by radical-mediated deoxygenation of the resulting tertiary alcohol.Keywords
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