Synthesis, Resolution, and Applications of 2,2‘-Bis(diphenylphosphino)-3,3‘- binaphtho[2,1-b]furan

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...

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Bibliographic Details
Published in:Organic letters 2000-09, Vol.2 (18), p.2817-2820
Main Authors: Andersen, Neil G, Parvez, Masood, Keay, Brian A
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006238+