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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 6
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Original Articles

Enantioselective Synthesis of Chiral Propargylic Alcohols Catalyzed by Bifunctional Zinc-Based Complexes

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Pages 775-783 | Received 17 Nov 2009, Published online: 11 Nov 2011

REFERENCES

  • Barouh , V. ; Dall , H. ; Patel , D. ; Hite , G. Stereochemical aspects of antihistamine action, 4: Absolute configuration of carbinoxamine antipodes . J. Med. Chem. 1971 , 14 , 834 .
  • Trost , B. M. ; Krische , M. J. Palladium-catalyzed enyne cycloisomerization reaction in an asymmetric approach to the picrotoxane sesquiterpenes, 2: Second-generation total syntheses of corianin, picrotoxinin, picrotin, and methyl picrotoxate . J. Am. Chem. Soc. 1999 , 121 , 6131 .
  • Cozzi , P. G. ; Hilgraf , R. ; Zimmermann , N. Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond . Eur. J. Org. Chem. 2004 , 4095 .
  • Lu , G. ; Li , Y. M. ; Li , X. S. ; Chan , A. S. C. Synthesis and application of new chiral catalysts for asymmetric alkynylation reactions . Coord. Chem. Rev. 2005 , 249 , 1736 .
  • Pu , L. Asymmetric alkynylzinc additions to aldehydes and ketones . Tetradedron 2003 , 59 , 9873 .
  • Trost , B. M. ; Weiss , A. H. The enantioselective addition of alkyne nucleophiles to carbonyl groups . Adv. Synth. Catal. 2009 , 351 , 963 .
  • Mao , J. C. ; Xie , G. L. Novel chiral catalysts for asymmetric addition of terminal alkynes to aldehydes . Curr. Org. Chem. 2009 , 13 , 1553 .
  • Li , X. ; Lu , G. ; Kwok , W. H. ; Chan , A. S. C. Highly enantioselective alkynylzinc addition to aromatic aldehydes catalyzed by self-assembled titanium catalysts . J. Am. Chem. Soc. 2002 , 124 , 12636 .
  • Tyrrell , E. Asymmetric alkynylation reactions of aldehydes using a Zn(OTf)2-chiral ligand-base system . Curr. Org. Chem. 2009 , 13 , 1540 .
  • Takita , R. ; Yakura , K. ; Ohshima , T. ; Shibasaki , M. Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex . J. Am. Chem. Soc. 2005 , 127 , 13760 .
  • Hsieh , S. S. ; Gau , H. M. Asymmetric alkynyl additions to aldehydes catalyzed by tunable oxovanadium(V) complexes of Schiff bases of β-amino alcohols . Synlett. 2006 , 1871 .
  • Asano , Y. ; Hara , K. ; Ito , H. ; Sawamura , M. Enantioselective addition of terminal alkynes to aldehydes catalyzed by a Cu(I)-TRAP complex . Org. Lett. 2007 , 9 , 3901 – 3904 .
  • Li , Z. B. ; Liu , T. D. ; Pu , L. Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes. J. Org. Chem. 2007, 72, 4340.
  • Xu , Z. ; Mao , J. ; Zhang , Y. Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine–titanium complex . Org. Biomol. Chem. 2008 , 6 , 1288 .
  • Mao , J. ; Wan , B. ; Wu , F. ; Lu , S. Readily available sulfamide-amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(O i Pr)4 . Chirality 2005 , 17 , 245 .
  • Xu , Z. ; Wu , N. ; Ding , Z. ; Wang , T. ; Mao , J. ; Zhang , Y. L-Proline-derived teriary amino alcohol as a new chiral ligand for enantioselective alkynylation of aldehydes . Tetrahedron Lett. 2009 , 50 , 926 .
  • Mao , J. ; Guo , Jun. Enantioselective addition of methyl propilate to aldehydes catalyzed by oxazolidine-titantium complex . Synlett. 2009 , 2295 .
  • Mao , J. ; Bao , Z. ; Guo , J. ; Ji , S. Enantioselective alkynylation of aromatic and heteroaromatic aldehydes catalyzed by resin-supported oxazolidine–titanium complexes . Tetrahedron 2008 , 64 , 9901 .
  • Xu , Z. ; Mao , J. ; Zhang , Y. (1S, 2R)-2-Amino-1,2-diphenylethanol as a new chiral ligand for enantioselective alkynylation of aldehydes . Catal. Commun. 2008 , 10 , 113 .
  • Shibasaki , M. ; Kanai , M. Multifunctional asymmetric catalysis . Chem. Pharm. Bull. 2001 , 49 , 511 .
  • Gröger , H. The development of new monometallic bifunctional catalysts with Lewis acid and Lewis base properties, and their application in asymmetric cyanation reactions . Chem. Eur. J. 2001 , 7 , 5246 .
  • Shibasaki , M. ; Kanai , M. ; Funabashi , K. Recent progress in asymmetric two-center catalysis . Chem. Commun. 2002 , 1989 .
  • Kang , Y. F. ; Liu , L. ; Wang , R. ; Yan , W. ; Zhou , Y. F. The use of bifunctional catalyst systems in the asymmetric addition of alkynylzinc to aldehydes . Tetrahedron: Asymmetry 2004 , 15 , 3155 .

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