A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties

Andrei S Batsanov; Christophe Grosjean; Thorben Schütz; Andrew Whiting

doi:10.1021/jo0708792

A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties

J Org Chem. 2007 Aug 3;72(16):6276-9. doi: 10.1021/jo0708792. Epub 2007 Jul 12.

Authors

Andrei S Batsanov¹, Christophe Grosjean, Thorben Schütz, Andrew Whiting

Affiliation

¹ Chemistry Department, Durham University, Science Laboratories, South Road, Durham, U.K.

PMID: 17628110
DOI: 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boron / chemistry
Boron Compounds / chemistry*
Chemistry, Organic / methods*
Chromatography, High Pressure Liquid
Crystallography, X-Ray
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Conformation
Proline / chemistry*
Sparteine / chemistry*
Stereoisomerism

Substances

Boron Compounds
Sparteine
Proline
Boron