Abstract
Financial support from the Ministerio de Ciencia e Innovacion (MICINN) of Spain (Project Nos. CTQ2007-65218, CTQ2011-24165, Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (PROMETEO/2009/0349 and FEDER), and the Universidad de Alicante is acknowledged.
Highlights
Binaphthyl derivative 11 has revealed to be very active as catalyst in the lithiation process at room temperature, and has allowed the preparation of the alcohol derivatives with enantioselectivities up to 50%
Organolithium compounds constitute a unique class of reagents due to their characteristic reactivity, the functionalized organolithiums and the polylithium synthons being of special interest in organic synthesis.[4,5,6,7,8,9,10,11,12,13,14,15]
We have shown that different binaphthyl derivatives are effective catalysts in the arene-lithiation process of 2-chloro-1-phenylpropane 2
Summary
The formation of carbon–carbon bonds represents a key step in the synthesis of many organic products, and organometallic reagents have become a fundamental tool in order to accomplish this type of transformation.[1,2,3] Organolithium compounds constitute a unique class of reagents due to their characteristic reactivity, the functionalized organolithiums and the polylithium synthons being of special interest in organic synthesis.[4,5,6,7,8,9,10,11,12,13,14,15] Deprotonation and halogen/lithium exchange, employing commercially available organolithium reagents, are conventionally the main routes for the preparation of other organolithium reagents. Treatment of chloride 2 with an excess of lithium, in the presence of the electrophile (i.e. pentan-3-one), at room temperature in dry THF did not produce the corresponding organolithium intermediate, and the expected alcohol 3 was not obtained after hydrolysis.
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