✦ LIBER ✦

Homo- and Heterocomplexes of Sodium and Lithium Amides—Structures in Solution

✍ Scribed by Anna Johansson; Öjvind Davidsson

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 111 KB
Volume: 7
Category: Article
ISSN: 0947-6539
DOI: 10.1002/1521-3765(20010817)7:16<3461::aid-chem3461>3.0.co;2-q

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✦ Synopsis

Addition of the chiral amine (S)-methyl(1-phenyl-2-pyrrolidinoethyl)-[ 15 N]amine (1) to a large excess of nBuNa resulted in the formation of a mixed sodium amide/nBuNa complex. This is the first observation of such a complex. Addition of nBuLi to the chiral sodium amide dimer 3 gave a new mixed lithium/sodium amide 5. The use of 15 N, 6 Li coupling constants showed that the lithium in 5 occupied the tetracoordinated site. The use of chiral sodium amide 3 in the desymmetrization of cyclohexene oxide gave a modest enantiomeric excess (ee) of 37%. The corresponding lithium amide gave an ee of 70 % of the same enantiomer. This is the first example of the comparison of asymmetric induction by sodium as cation with that of lithium.

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