Manufacturing method of organoboron compound

Details Manufacturing method of organoboron compound Manufacturing method of organoboron compound

2008-04-10

2010-11-23

Sullivan, Daniel M (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

C568S001000

Reexamination Certificate

active

07838697

ABSTRACT:
A manufacturing method for one of, or a mixture of, an optically active allylboron compound and racemic or optically active boryl cyclopropane, including a coupling reaction, in the presence of a catalyst, between allyl compound and diboron compound. It is preferred that a copper (I) complex is used as the catalyst. It is preferred that a counterion of the copper (I) complex is an alkoxide or a hydride. It is preferred that the copper (I) complex has a phosphine ligand. It is preferred that the phosphine ligand is a chiral phosphine ligand.

REFERENCES:
Ito et al, {Copper-Catalyzed -Selective and Stereospecific Substitution Reaction of Allylic Carbonates with Diboron: Efficient Route to Chiral Allylboron Compounds, Journal of the American Chemical Society (2005), 127(46), 16034-16035}.
Kabalka et al., {Pd-Catalyzed Cross-Coupling of Baylis-Hillman Acetate Adducts with Bis(pinacolato)diboron: An Efficient Route to Functionalized Allyl Borates, Journal of Organic Chemistry (2004), 69(17), 5807-5809}.
Ito et al., {Copper-Catalyzed Enantioselective Substitution of Allylic Carbonates with Diboron: An Efficient Route to Optically Active -Chiral Allylboronates, Journal of the American Chemical Society (2007), 129(48), 14856-14857}.
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Hildebrand et al., “A Novel, Stereocontrolled Synthesis of 1,2-trans-Cyclopropanes: Cyclopropyl Boronate Esters as Partners in Suzuki Couplings with Aryl Halides,” Synlett, vol. 41, pp. 893-894, 1996.
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Rubina et al., “Catalytic Enantioselective Hydroboration of Cyclopropenes,” Journal of the American Chemical Society, vol. 125, No. 24, pp. 7198-7199, 2003.

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