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Org Lett. 2012 Aug 17;14(16):4238-41. doi: 10.1021/ol301935q. Epub 2012 Aug 7.

Synthesis, reactivity, and resolution of a C2-symmetric, P-stereogenic benzodiphosphetane, a building block for chiral bis(phosphines).

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  • 16128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, United States.


Although the pyramidal inversion barriers in diphosphines (R(2)P-PR(2)) are similar to those in phosphines (PR(3)), P-stereogenic chiral diphosphines have rarely been exploited as building blocks in asymmetric synthesis. The synthesis, reactivity, and resolution of the benzodiphosphetane trans-1,2-(P(t-Bu))(2)C(6)H(4) are reported. Alkylation with MeOTf followed by addition of a nucleophile gave the useful C(2)-symmetric P-stereogenic ligand BenzP* and novel analogues.

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