Mixed aggregates of an alkyl lithium reagent and a chiral lithium amide derived from N-ethyl-O-triisopropylsilyl valinol

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作者：
Su, Chicheung [1 ]
Hopson, Russell [1 ]
Williard, Paul G. [1 ]
机构：
[1] Su, Chicheung
[2] Hopson, Russell
[3] Williard, Paul G.
来源：
Williard, P.G. (pgw@brown.edu) | 1600年 / American Chemical Society卷 / 135期
关键词：
The crystal structure of a mixed aggregate containing lithiated (S)-N-ethyl-3-methyl-1-(triisopropylsilyloxy)butan-2-amine derived from (S)-valinol and cyclopentyllithium is determined by X-ray diffraction. The mixed aggregate adopts a ladder structure in the solid state. The ladder-type mixed aggregate is also the major species in a toluene-d8 solution containing an approximately 1:1 molar ratio of the lithiated chiral amide to cyclopentyllithium. A variety of NMR experiments including diffusion-ordered NMR spectroscopy (DOSY) with diffusion coefficient-formula (D-FW) weight correlation analyses and other one- and two-dimensional NMR techniques allowed us to characterize the complex in solution. Solution state structures of the mixed aggregates of n-butyl; sec-butyllithium; isopropyllithium with lithiated (S)-N-ethyl-3-methyl-1-(triisopropylsilyloxy)butan-2-amine are also reported. Identical dimeric; ladder-type; mixed aggregates are the major species at a stoichiometric ratio of 1:1 lithium chiral amide to alkyllithium in toluene-d8 solution for all of the different alkyllithium reagents. © 2013 American Chemical Society;
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页码：14367 / 14379
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