Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza??Michael Reaction

D Enders, DP Goeddertz, C Beceno…

Index: Enders, Dieter; Goeddertz, Dominik P.; Beceno, Christian; Raabe, Gerhard Advanced Synthesis and Catalysis, 2010 , vol. 352, # 17 p. 2863 - 2868

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Citation Number: 32

Abstract

Abstract The domino Mannich/aza-Michael reaction of γ-malonate-substituted α, β- unsaturated esters with N-protected arylaldimines has been achieved. Catalyzed by bifunctional thioureas, 2, 5-cis-configured polysubstituted pyrrolidines are obtained in good to excellent yields (76–99%), enantioselectivities (75–94%) and excellent diastereoselectivities (de> 95%). The pure stereoisomers are available by crystallization ...

~83%

… -carbon bond-forming enantioselective synthesis of chiral ...

[Shintani, Ryo; Okamoto, Kazuhiro; Otomaru, Yusuke; Ueyama, Kazuhito; Hayashi, Tamio Journal of the American Chemical Society, 2005 , vol. 127, # 1 p. 54 - 55]

Synthesis of [2H, 13C]??Labelled Diallylmalonates− Useful Pr...

[Bray, Katharine L.; Lloyd-Jones, Guy C. European Journal of Organic Chemistry, 2001 , # 9 p. 1635 - 1642]

Highly chemoselective oxidation of dithioester Enethiolates ...

[Herrmann,J.L. et al. Tetrahedron Letters, 1973 , p. 4711 - 4714]

Reactivity of Electrophilic Allyl Halides

[Verhe, R.; De Kimpe, N.; De Buyck, L.; Courtheyn, D.; Caenegem, L. Van; Schamp, N. Bulletin des Societes Chimiques Belges, 1983 , vol. 92, # 4 p. 371 - 396]