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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 14
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Original Articles

Asymmetric Addition of Diethylzinc to Ketones promoted by Tartaric Acid Derivatives

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Pages 2374-2384 | Received 19 Apr 2007, Published online: 11 Jul 2008

REFERENCES

  • Fuji , K. Asymmetric creation of quaternary carbon centers . Chem. Rev. 1993 , 93 , 2037 – 2066 ; (b) Corey, E. J.; Guzmán, A. The catalytic enantioselective construction of molecules with quaternary carbon stereocenters. Angew. Chem., Int. Ed. Engl. 1998, 37, 388–401; (c) Pu, L. Asymmetric alkynylzinc additions to aldehydes and ketones. Tetrahedron 2003, 59, 9873–9886; (d) Ramón, D. J.; Yus, M. Chiral tertiary alcohols made by catalytic enantioselective addition of unreactive zinc reagents to poorly electrophilic ketones. Angew. Chem., Int. Ed. Engl. 2004, 43, 284–287 .
  • Knochel , P. ; Perea , J. J. A. ; Jones , P. Organozinc mediated reactions . Tetrahedron 1998 , 54 , 8275 – 8319 ; (b) Knochel, P. Stereoselective reactions mediated by functionalized diorganozincs. Synlett 1995, 393–403; (c) Knochel, P.; Singer, R. D. Preparation and reactions of polyfunctional organozinc reagents in organic synthesis. Chem. Rev. 1993, 93, 2117–2188 .
  • Dosa , P. I. ; Fu , G. C. Catalytic asymmetric addition of ZnPh2 to ketones: Enantioselective formation of quaternary stereocenters . J. Am. Chem. Soc. 1998 , 120 , 445 – 446 .
  • Ramón , D. J. ; Yus , M. First enantioselective addition of dialkylzinc to ketones promoted by titanium(IV) derivatives . Tetrahedron Lett. 1998 , 39 , 1239 – 1242 ; (b) Ramón , D. J. ; Yus , M. First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives . Tetrahedron 1998 , 54 , 5651 – 5666 .
  • García , C. ; LaRochelle , L. K. ; Walsh , P. J. A practical catalytic asymmetric addition of alkyl groups to ketones . J. Am. Chem. Soc. 2002 , 124 , 10970 – 10971 .
  • Yus , M. ; Ramón , D. J. ; Prieto , O. Highly enantioselective addition of dialkylzinc reagents to ketones promoted by titanium tetraisopropoxide . Tetrahedron: Asymmetry 2002 , 13 , 2291 – 2293 .
  • Yus , M. ; Ramón , D. J. ; Prieto , O. (−)-Frontalin: Synthesis using the catalytic enantioselective addition of dimethylzinc to a ketone . Eur. J. Org. Chem. 2003 , 2745 – 2748 .
  • García , C. ; Walsh , P. J. Highly enantioselective catalytic phenylation of ketones with a constrained geometry titanium catalyst. Org. Lett. 2003, 5, 3641–3644.
  • Prieto , O. ; Ramón , D. J. ; Yus , M. Highly enantioselective arylation of ketones . Tetrahedron: Asymmetry 2003 , 14 , 1955 – 1957 .
  • Yus , M. ; Ramón , D. J. ; Prieto , O. Synthesis of new C2-symmetrical bis(hydroxycamphorsulfonamide) ligands and their application in the enantioselective addition of dialkylzinc reagents to aldehydes and ketones . Tetrahedron: Asymmetry 2003 , 14 , 1103 – 1114 .
  • de Parrodi , C. A. ; Walsh , P. J. Trans-1,2-diaminocyclopentane-based catalyst for the asymmetric addition of alkyl-, aryl-, and vinyl groups to ketones . Synlett 2004 , 2417 – 2420 .
  • Forrat , V. J. ; Ramón , D. J. ; Yus , M. Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2-isoborneolsulfonylaminocyclohexane-catalyzed addition of organozincs to ketones . Tetrahedron: Asymmetry 2005 , 16 , 3341 – 3344 .
  • Jeon , S. J. ; Li , H. M. ; García , C. ; LaRochelle , L. K. ; Walsh , P. J. Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones . J. Org. Chem. 2005 , 70 , 448 – 455 .
  • Jeon , S. J. ; Li , H. M. ; Walsh , P. J. A green chemistry approach to a more efficient asymmetric catalyst: Solvent-free and highly concentrated alkyl additions to ketones . J. Am. Chem. Soc. 2005 , 127 , 16416 – 16425 .
  • Hui , A. L. ; Zhang , J. T. ; Fan , J. M. ; Wang , Z. Y. A new chiral sulfonamide ligand based on tartaric acid: Synthesis and application in the enantioselective addition of diethylzinc to aldehydes and ketones . Tetrahedron: Asymmetry 2006 , 17 , 2101 – 2107 .
  • For the synthesis of chiral amine 11 and 16 from L-tartaric acid, see (a) Nagel , U. ; Kinzel , E. ; Andrade , J. ; Prescher , G. Enantioselective catalysis .4. synthesis of N-substituted (R, R)-3,4-bis (diphenylphosphino) pyrrolidines-the use of their rhodium complexes for the asymmetric hydrogenation of alpha-(acylamino) acrylic acid derivatives . Chem. Ber. 1986 , 119 , 3326 – 3343 ; (b) Caldwell, C. G.; Chen, P.; He, J. F.; Parmee, E. R.; Leiting, B.; Marsilio, F.; Patel, R. A.; Wu, J. K.; Eiermann, G. J.; Petrov, A.; He, H. B.; Lyons, K. A.; Thornberry, N. A.; Weber, A. E. Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 1265–1268; (c) Nagel, U. Asymmetric hydrogenation of α-(acetylamino)cinnamic acid with a novel rhodium complex: The design of an optimal ligand. Angew. Chem. Int. Ed. Engl. 1984, 23, 435–436; (d) Siedlecka, R.; Wojaczyńska, E.; Skarżewski, J. Chiral pyrrolidine thioethers: Effective nitrogen–sulfur donating ligands in palladium-catalyzed asymmetric allylic alkylations. Tetrahedron: Asymmetry 2004, 15, 1437–1444; (e) Ryan, K.; Gershell, L. J.; Still, W. C. A synthetic receptor motif designed for extended peptide conformations. Tetrahedron 2000, 56, 3309–3318; (f) Skarżewski, J.; Gupta, A. Synthesis of C2-symmetric primary vicinal diamines: Double stereospecific mitsunobu reaction on the heterocyclic diols derived from tartaric acid. Tetrahedron: Asymmetry 1997, 8, 1861–1867; (g) Kuppert, D.; Sander, J.; Roth, C.; Wörle, M.; Weyhermüller, T.; Reiss, G. J.; Schilde, U.; Müller, I.; Hegetschweiler, K. The coordination chemistry of cis-3,4-diaminopyrrolidine and related polyamines. Eur. J. Inorg. Chem. 2001, 2525–2542 .
  • Balsells , J. ; Walsh , P. J. Design of diastereomeric self-inhibiting catalysts for control of turnover frequency and enantioselectivity. J. Am. Chem. Soc. 2000, 122, 3250–3251.

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