New, Improved Procedure for the Synthesis of Structurally Diverse N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides
- 1 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (11), 4576-4578
- https://doi.org/10.1021/jo030032f
Abstract
Selective, direct ortho magnesiation of (S)-2,2‘-bis(isopropoxycarbonyl)-1,1‘-binaphthyl (6) has been achieved under mild conditions, using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2]. In combination with the subsequent reaction with the appropriate electrophiles, bromine and iodine, this method constitutes a key step in establishing a new and concise synthetic route to a wide variety of N-spiro C2-symmetric chiral quaternary ammonium bromides of type 1.Keywords
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