Iron-catalyzed allylic alkylation

Details Iron-catalyzed allylic alkylation Iron-catalyzed allylic alkylation

2006-08-25

2009-02-03

Puttlitz, Karl J (Department: 1621)

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

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

07485744

ABSTRACT:
A method for performing an iron-catalyzed allylic alkylation includes the preparation of a reaction mixture obtainable from (i) an allylic substrate with the structural element C═C—C—X, wherein X comprises a leaving group that represents a carbonate, (ii) an active Fe(-II) catalyst complex, (iii) at least one ligand, (iv) at least one solvent, and (v) a nucleophile or pronucleophile.

REFERENCES:
Zhou et al. ,J. Org. Chem., 1988, 53, 4421-4422.
Xu et al., J. Org. Chem., 1987, 52, 974-977.
Plietker et al., Angewandte Chemie, International Edition (2006), 45(9), 1469-1473.
Ladoulis, Sandra J. et al., “Iron-Catalyzed 1-19 Allylic Alkylation,” Journal of Organometallic Chemistry, Bd. 285, 1985, C13-C16, XP002416506, Tab. 1.
Yamaguchi, H., et al.: “Synthesis of planar chiral η3-allyldicarbonylnitrosyliron complexes and sterochemistry of the complex . . . ” In: J. of Organometallic Chemistry, 554,(1998) pp. 167-170.
Silverman, G.S., et al.: “Iron-Promoted Allylic Alkylation: Regiochemical Sterochemical, and Mechanistic Aspects.” In: Organometallics, 1986, 5, pp. 2117-2124.
Itoh, K., et al.: “Conjugate addition of allylic groups to a α β-unsaturated carbonyl compounds via . . . ” In: J. of Organom. Chemistry, 473, 1994, pp. 215-224.
Davies, S.G., et al.: “The use of [Fe(CO)3NO] for the carbonylation of primary, secondary and allylic halides.” In: J. of Organom. Chemistry, 386, 1990, pp. 195-201.
Eberhardt, Udo, et al.: “Über die stereoselektive Bildung von syn- und anti-Dicarbonyl . . . ” In: Chem. Ber., 1988, 121, pp. 1531-1534.
Nakanishi, Saburo, et al.: “Animation of (η3-Allyl) dicarbonylnitrosyliron Complexes . . . ” In.: Synthesis, 1998, pp. 1735-1741.
Nakanishi, Saburo, et al.: “A Convenient Synthesis of β,γ-Unsaturated Carboxylic . . . ” In: Synthesis, 1994, pp. 609-612.
Zhou, B., et al.: “Studies on the Enantioselectivity in Bu4N[Fe(CO)3NO]-Catalyzed Nucleophilic . . . ” In: J. Org. Chem., 1988, 53, pp. 4419-4421.
Nakanishi, Saburo, et al.: “Preparation, Ligand Substitution, and Structural Stability of . . . ” In: Bull. Chem. Soc. Jpn. 71, 1998, pp. 403-412.
Itoh, K., et al.: “Preparation and Reactivities of (η3-1-and 2-Trimethylsiloxyallyl)Fe(CO)2NO Complexes . . . ” In: Bull. Chem. Soc. Jpn, 64, 1991, pp. 2965-2977.
Xu, Yuanyao, et a l.: “on the Regio-and Stereoselectivity of . . . ” In: J. Org. Chem. 52, 1987, pp. 974-977.
Nakanashi, et al.: CO Insetion of (η3-allyl)Fe(CO)2(NO) Complexes by Diphosphines In: Organometallics, 15, 1996, pp. 5432-5435.

Affiliated with

Also associated with

Rating

Iron-catalyzed allylic alkylation does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Iron-catalyzed allylic alkylation, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Iron-catalyzed allylic alkylation will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4133844