Diastereoselective Addition of Chlorotitanium Enolate Derived from 2′-Hydroxypropiophenone to Aldehydes

REFERENCES

• Itoh , Y. ; Yamanaka , M. ; Mikami , K. Direct generation of Ti-enolate of α-CF3 ketone: Theoretical study and high-yielding and diastereoselective aldol reaction . J. Am. Chem. Soc. 2004 , 126 , 13174 .
   PubMed Web of Science ®Google Scholar
• Franck , X. ; Seon-Meniel , B. ; Figadere , B. Highly diastereoselective aldol reaction with α-CF3-substituted enolates . Angew. Chem. Int. Ed. 2006 , 45 , 5174 .
   PubMed Web of Science ®Google Scholar
• Solsona , J. G. ; Nebot , J. ; Roma , P. ; Urpi , F. Highly stereoselective aldol reaction based on titanium enolates from (S)-1-benzyloxy-2-methyl-3-pentanone . J. Org. Chem. 2005 , 70 , 6533 .
   PubMed Web of Science ®Google Scholar
• Gawas , D. ; Kazmaier , U. Highly diastereoselective anti-aldol reactions of glycolate titanium enolates . J. Org. Chem. 2009 , 74 , 1788 .
   PubMed Web of Science ®Google Scholar
• Mahrwald , R. Diastereoselection in lewis acid–mediated aldol additions . Chem. Rev. 1999 , 99 , 1095 .
   PubMed Web of Science ®Google Scholar
• Solsona , J. G. ; Romea , P. ; Urpi , F. ; Vilarrasa , J. Highly stereoselective aldol reactions of titanium enolates from lactate-derived chiral ketones . Org. Lett. 2003 , 5 , 519 .
   PubMed Web of Science ®Google Scholar
• Luke , G. P. ; Morris , J. Titanium- and boron-mediated aldol reactions of β-hydroxy ketones. J. Org. Chem. 1995, 60, 3013
   Web of Science ®Google Scholar
• Ghosh , A. K. ; Liu , C. Enantioselective total synthesis of (+)-amphidinolide T1 . J. Am. Chem. Soc. 2003 , 125 , 2374 .
   PubMed Web of Science ®Google Scholar
• Crimmmins , M. T. ; Caussanel , F. Enantioselective total synthesis of FD-891 . J. Am. Chem. Soc. 2006 , 128 , 3128 .
   PubMed Web of Science ®Google Scholar
• Nebot , J. ; Figueras , S. ; Romea , P. ; Urpi , F. ; Ji , Y. Stereoselective titanium-mediated aldol reaction of (s)-2-tert-butyldimethyloxy-3-pentanone . Tetrahedron 2006 , 62 , 11090 .
   Web of Science ®Google Scholar
• Ortz , A. ; Sabala , R. ; Sansinenea , E. ; Bernes , S. Attempts towards the synthesis of feigrisolide B . Lett. Org. Chem. 2007 , 4 , 465 .
   Web of Science ®Google Scholar
• Figueras , S. ; Martin , R. ; Romea , P. ; Urpi , F. ; Vilarrasa , J. Highly stereoselective aldol reactions of titanium enolates from ethyl α –dilylocyalkyl ketones . Tetrahedron Lett. 1997 , 38 , 1637 .
   Web of Science ®Google Scholar
• Tiecco , M. ; Testaferri , L. ; Marini , F. ; Sternativo , S. ; Santi , C. O. ; Bagnoli , L. ; Temperini , A. Asymmetric aldol reactions from titanium enolates of α-seleno ketones and esters . Tetrahedron: Asymmetry 2004 , 15 , 783 .
   Web of Science ®Google Scholar
• Nakamura , S. ; Hayakawa , T. ; Nishi , T. ; Watanabe , Y. ; Toru , T. Stereoselective aldol reaction of α-seleno carbonyl compounds: Preparetion of (Z)-α,β-unsaturated carbonyl compounds . Tetrahedron 2001 , 57 , 6703 .
   Web of Science ®Google Scholar
• Lee , Y.-S. ; Choung , W.-K. ; Kim , K. H. ; Kang , T. W. ; Ha , D.-C. A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone . Tetrahedron 2004 , 60 , 867 .
   Web of Science ®Google Scholar
• Li , H.-J. ; Tian , H.-Y. ; Wu , Y.-C. ; Chen , Y.-J. ; Liu , L. ; Wang , D. ; Li , C.-J. Synthesis of acetonides from epoxides catalyzed by erbium(III) triflate . Adv. Synth. Catal. 2005 , 347 , 1247 .
   Web of Science ®Google Scholar
• Bernard , A. ; Cavicchioli , M. ; Marchionni , C. ; Potenza , D. ; Scolastico , C. Titanium ate enolate complexes: An NMR study . J. Org. Chem. 1994 , 59 , 3690 .
   Web of Science ®Google Scholar
• Moreira , I. de P. R. ; Bofill , J. M. ; Anglada , J. M. ; Solsona , J. G. ; Nebot , J. ; Romea , P. ; Urpi , F. Synthetic collagen heterotrimers: structural mimics of wild-type and mutant collagen type I . J. Am. Chem. Soc. 2008 , 130 , 3242 .
   PubMed Web of Science ®Google Scholar
• Otero , J. Stereoselective aldol reactions in the synthesis of polyketide natural products . In Modern Cabonyl Chemistry ; VCH : Weinheim , 2000 ; p. 249 .
   Google Scholar
• Evans , D. A. ; Urpi , F. ; Somers , T. C. ; Clark , J. S. ; Bilodeau , M. T. New procedure for the direct generation of titanium enolates: Diastrerosrlectitive bond constructions with representative electrophiles . J. Am. Chem. Soc. 1990 , 112 , 8215 .
   Web of Science ®Google Scholar
• Crimmins , M. T. ; King , B. W. ; Tabet , E. A. Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and lewis acid stoichiometry . J. Am. Chem. Soc. 1997 , 119 , 7883 .
   Web of Science ®Google Scholar
• Hermange , P. ; Dau , M. E. T. H. ; Retailleau , P. ; Dodd , R. H. Highly diastereoselective three-component vinylogous mannich reaction between isoquinolines, Acyl/Sulfonyl chlorides, and silyloxyfurans . Org. Lett. 2009 , 11 , 4044 .
   PubMed Web of Science ®Google Scholar
• Harrison , C. R. Transient titanium enolate aldol condensations . Tetrahedron Lett. 1987 , 28 , 4135 .
   Web of Science ®Google Scholar
• Matsumura , Y. ; Nishimura , M. ; Hiu , H. Dependence of the reactivities of titanium enolates on how they are generated: Diastereoselective coupling of phenylacetic acid esters using titanium tetrachloride . J. Org. Chem. 1996 , 61 , 2809 .
   PubMed Web of Science ®Google Scholar