Krief-synthesis

A. Bureau, L. Heveri, W. Dumont, A. Cravador u. A. Krief, Synthesis 1979, 877ff. 

Krief, A. Synthesis and Synthetic Applications of 1-Metallo-l-Selenocyclopropanes and -cyclobutanes and Related 1-Metallo-l-silyl-cyclopropanes. 135, 1-75 (1986). 

Denis Magnane Van Eenoo Krief Nouv. J. Chim. 1979, 3, 705. For other silyl reagents, see Reetz Plachky Synthesis 1976,199 Dervan Shippey J. Am. Chem. Soc. 1976,98,1265 Caputo Mangoni Neri Palumbo Tetrahedron Lett. 1981, 22, 3551. 

Dubinsky L, Jarosz LM, Amara N, Krief P, Kravchenko VV, Krom BP, Meijler MM (2009) Synthesis and validation of a probe to identify quorum sensing receptors. Chem Commun 47 7378... 

A. Krief, A.-M. Laval, Ortho-Nitrophenyl Selenocyanate, a Valuable Reagent in Organic Synthesis Application to One of the Most Powerful Routes to Terminal Olefins from Primary-Alcohols (The Grieco-Sharpless Olefination Reaction) and to the Regioselective Isomerization of Allyl Alcohols), ... 

In the newest method of synthesis, which allows the large-scale production of SeMet, L-Met is first converted to the methyl-methionium derivative, which is hydrolyzed to homoserine and converted to a-amino-y-butyrolac-tone. The latter is reacted with HBr to 2-amino-4-bromobutanoic acid, from which L-SeMet is obtained on reaction with LiSeCH3 (Koch and Burchardt, 1993 Krief et al., 1994). 

When the alkene trap is 1,1-disubstituted, cyclisation of a tertiary benzylic organolithium gives a product with two adjacent quaternary centres. Krief applied this type of cyclisation to the synthesis of cuparene 244136 using a different disconnection from the one used by Bailey (above). Though it is irrelevant to the synthesis of cuparene, the cyclisation of 257 to 258 is also stereoselective and produces a single stereoisomer of 259 on carbonation of the cyclised organolithium. The tertiary organolithium is too basic to cyclise in THF and in this solvent... 

A. Krief in Comprehensive Organic Synthesis (Eds. B. M. Trost and I. Fleming), Pergamon Press, Oxford, 1991. 

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