Synthesis 2016; 48(16): 2659-2663
DOI: 10.1055/s-0035-1561854
special topic
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of (S)- and (R)-tert-Butylmethylphosphine–Borane: A Novel Entry to Important P-Stereogenic Ligands

Ernest Salomó ◊�
a  Institute of Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, 08028, Spain
,
Sílvia Orgué ◊�
a  Institute of Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, 08028, Spain
,
Antoni Riera*
a  Institute of Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, 08028, Spain
b  Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, 08028, Spain   Email: antoni.riera@irbbarcelona.org   Email: xavier.verdaguer@irbbarcelona.org
,
Xavier Verdaguer*
a  Institute of Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac 10, 08028, Spain
b  Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, 08028, Spain   Email: antoni.riera@irbbarcelona.org   Email: xavier.verdaguer@irbbarcelona.org
› Author Affiliations
Further Information

Publication History

Received: 15 January 2016

Accepted: 26 February 2016

Publication Date:
22 March 2016 (eFirst)

◊� These authors contributed equally to the present work.

Abstract

A novel one-pot reductive methodology for the synthesis of optically pure tert-butylmethylphosphine–borane is reported. The preparation uses as the starting material tert-butylmethylphosphinous acid–borane, which is available in both enantiomeric forms from cis-1,2-aminoindanol and tert-butyldichlorophosphine. The process is based on the reduction of a mixed anhydride, the configurational stability of which has been studied in several solvents and temperatures. Tetrabutylammonium borohydride was the best reducing agent allowing for the development of a practical process. To demonstrate the utility of the new methodology, the product obtained in this manner was used in the preparation of Quinox-P*.

 
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