A (−)-Sparteine-Directed Highly Enantioselective Synthesis of Boroproline. Solid- and Solution-State Structure and Properties
- 12 July 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (16), 6276-6279
- https://doi.org/10.1021/jo0708792
Abstract
A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.Keywords
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