Synthesis, resolution, and applications of 2, 2'-bis(diphenylphosphino)-3,3'- binaphtho[2,1-b]furan.
[structure: see text] A short five-step synthesis of (+/-)-2,2'-bis(diphenylphosphino)-3, 3'-binaphtho[2,1-b]furan (BINAPFu, 1) starting from 2-naphthoxyacetic acid is reported. The resolution of BINAPFu 1 was possible using our newly developed resolution procedure for phosphines wherein (1S)-camphorsulfonyl azide was used to prepare the bisphosphinimine of BINAPFu via the Staundinger reaction. BINAPFu consistently outperformed BINAP in an asymmetric Heck reaction between 2,3-dihydrofuran and phenyl triflate.
Andersen
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NG
Department of Chemistry, University of Calgary, Calgary, Alberta, Canada T2N 1N4.
Parvez
M
M
Keay
B A
BA