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Bisphosphine-Catalyzed Mixed Double-Michael Reactions: Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines
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Abstract
Bisphosphine-catalyzed mixed double-Michael reactions have been developed to afford β-amino carbonyl derivatives of oxazolidines, thiozolidines, and pyrrolidines in excellent yields and with high diastereoselectivities. Efficient reactions between amino-acid-derived pronucleophiles, such as β-amino alcohols, β-amino thiols, and γ-amino diesters, as Michael donors and electron-deficient acetylenes, such as propiolates, acetylacetylene, and tosylacetylene, as Michael acceptors provided access to azolidines containing both diversity of substituents and asymmetry. This methodology
the first examples of mixed double-Michael reactions of acetylenesis operationally simple and involves mild conditions. Mechanistically, it constitutes a rare example of the anchimeric assistance of bisphosphines in organocatalysis.
Citing Articles
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This article has been cited by 18 ACS Journal articles (5 most recent appear below).
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Stereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1,2-Amino Alcohols
Amanda F. Ward and John P. WolfeOrganic Letters2011 Article ASAPStereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1,2-Amino Alcohols
Amanda F. Ward and John P. WolfeOrganic Letters2011 Article ASAPThe stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol derivatives. The transformations generate cis-disubstituted products with good to excellent ...
β-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes
Mathias J. Jacobsen, Erik Daa Funder, Jacob R. Cramer, and Kurt V. GothelfOrganic Letters2011 Article ASAPβ-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes
Mathias J. Jacobsen, Erik Daa Funder, Jacob R. Cramer, and Kurt V. GothelfOrganic Letters2011 Article ASAPA phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for various aryl, alkyl, and alkenyl aldehydes ...
Phosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans
Jian Hu, Yabing Wei, and Xiaofeng TongOrganic Letters2011 Article ASAPPhosphine-Catalyzed [3 + 2] Annulations of γ-Functionalized Butynoates and 1C,3O-Bisnucleophiles: Highly Selective Reagent-Controlled Pathways to Polysubstituted Furans
Jian Hu, Yabing Wei, and Xiaofeng TongOrganic Letters2011 Article ASAPIn this paper, a reagent-controlled [3 + 2] annulation of γ-functionalized butynoates 1 and 1C,3O-bisnucleophiles 2 is reported, which leads to three distinct furan skeletons 3–5. A PPh3 catalyst preferentially attached the β-position of 1a, facilitating ...
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History
- Published In Issue October 31, 2007
- Received May 24, 2007
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