ChemInform Abstract: Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition of 1,4-Bis(diphenylphosphinoyl)buta-1,3-diyne with Tethered Diynes. A Modular, Highly Versatile Single-Pot Synthesis of NU-BIPHEP Biaryl Diphosphines.

School of Natural Sciences, Chemistry, Newcastle University, Newcastle Upon Tyne, UK.
Organic Letters (Impact Factor: 6.36). 12/2007; 9(23):4925-8. DOI: 10.1021/ol702390p
Source: PubMed


Rhodium-catalyzed double [2 + 2 + 2] cycloaddition of 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne with tethered diynes provides a straightforward, single-pot procedure for the synthesis of a new class of tropos biaryl diphosphine, NU-BIPHEP. This methodology represents a significant improvement on existing multistep procedures. Enantiopure Lewis acid platinum complexes of these diphosphines are highly efficient catalysts for carbonyl-ene and Diels-Alder reactions, and ruthenium diphosphine-diamine complexes catalyze the asymmetric reduction of ketones to give ee's that rival those obtained with their BINAP counterpart.

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