A (−)-Sparteine-Directed Highly Enantioselective Synthesis of Boroproline. Solid- and Solution-State Structure and Properties

A (−)-Sparteine-Directed Highly Enantioselective Synthesis of Boroproline. Solid- and Solution-State Structure and Properties

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 yiel...

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Veröffentlicht in:Journal of organic chemistry 2007-08, Vol.72 (16), p.6276-6279
Hauptverfasser: Batsanov, Andrei S, Grosjean, Christophe, Schütz, Thorben, Whiting, Andrew
Format: Artikel
Sprache:eng
Schlagworte:
Boron - chemistry
Boron Compounds - chemistry
Chemistry
Chemistry, Organic - methods
Chromatography, High Pressure Liquid
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Conformation
Organic chemistry
Preparations and properties
Proline - chemistry
Sparteine - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0708792