Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.

Content Provider	Semantic Scholar
Author	Sun, Xing Huai Winemiller, Mark D. Xiang, Bosong Collum, David B.
Copyright Year	2001
Abstract	Low-temperature (6)Li, (13)C, and (15)N NMR spectroscopies reveal that mixtures of n-BuLi and (1R,2S)-R'(2)NCH(R)CH(Ph)OLi (ROLi; R = Ph or Me; R'(2)N = pyrrolidino or Me(2)N) in THF/pentane afford a (n-BuLi)(3)(ROLi) (3:1) mixed tetramer and a C(2)-symmetric (n-BuLi)(2)(ROLi)(2) (2:2) mixed tetramer depending on the proportions of the reactants. The corresponding (n-BuLi)(ROLi)(3) (1:3) mixed tetramer is not observed. ROLi-mediated additions of n-BuLi to benzaldehyde proceed with up to 21:1 enantiomeric ratios that depend on the n-BuLi/ROLi stoichiometries. The enantioselectivities are considered in light of a previously posited mechanism involving reaction via the C(2)-symmetric 2:2 mixed tetramer.
File Format	PDF HTM / HTML
DOI	10.1021/ja010136c
Alternate Webpage(s)	http://collum.chem.cornell.edu/publications/75.pdf
PubMed reference number	11506560
Alternate Webpage(s)	https://doi.org/10.1021/ja010136c
Journal	Medline
Volume Number	123
Issue Number	33
Journal	Journal of the American Chemical Society
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article