✦ LIBER ✦

Chiral diamines. Part 3: Effect of ligand structure on the enantioselective deprotonation of N-Boc-pyrrolidine with i-PrLi: a computational comparison of (−)-sparteine and (S,S)-1,2-bis(N,N-dimethylamino)cyclohexane

✍ Scribed by Kenneth B. Wiberg; William F. Bailey

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 320 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01353-8

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✦ Synopsis

The deprotonation N-Boc-pyrrolidine by i-PrLi-(S,S)-1,2-bis(N,N-dimethylamino)cyclohexane has been studied at the HF/3-21G and B3P86/6-31G* theoretical levels. The two lowest energy complexes of the N-Boc-pyrrolidine-i-PrLi-diamine ligand, as well as the transition states leading to proton transfer, were found to be similar in both geometry and energy in accord with experimental findings. The results are compared to those for the analogous but enantioselective (-)-sparteine-mediated deprotonation.