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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

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Catherine Smyth, Dr Ross Harrington, Emeritus Professor Bill Clegg

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Abstract

(Chemical Equation Presented) 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. © 2007 American Chemical Society.


Publication metadata

Author(s): Doherty S, Knight JG, Smyth CH, Harrington RW, Clegg W

Publication type: Letter

Publication status: Published

Journal: Organic Letters

Year: 2007

Volume: 9

Issue: 23

Pages: 4925-4928

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

URL: http://dx.doi.org/10.1021/ol702390p

DOI: 10.1021/ol702390p


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