Synthesis of Optically Pure Terminal Epoxide and 1,2‐Diol via Hydrolytic Kinetic Resolution Catalyzed by New Heterometallic Salen Complexes

References

• Ojima , I. 2000 . Catalytic Asymmetric Synthesis , 2nd Ed. Edited by: Ojima , I. New York : Wiley .
   Google Scholar
• Jacobsen , E. N. , Pfaltz and Yamamoto , A. H. 1999 . Comprehensive Asymmetric Catalysis Heidelberg : Springer .
   Google Scholar
• Shibasaki , M. , Kanai , M. and Funabashi , K. 2002 . Recent progress in asymmetric two‐center catalysis . Chem. Commun. , : 1989 – 1999 .
   PubMedGoogle Scholar
• Shibasaki , M. and Yoshikawa , N. 2002 . Lanthanide complexes in multifunctional asymmetric catalysis . Chem. Rev. , 102 : 2187 – 2210 .
   PubMed Web of Science ®Google Scholar
• Iida , T. , Yamamoto , N. , Matsunaga , S. , Woo , H.‐G. and Shibasaki , M. 1998 . Enantioselective ring opening of epoxides with 4‐methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1,2‐diol monoethers . Angew. Chem. Int. Ed. , 37 : 2223 – 2225 .
   PubMed Web of Science ®Google Scholar
• Matsunaga , S. , Yoshida , T. , Morimoto , H. , Kumagai , N. and Shibasaki , M. 2004 . Direct catalytic asymmetric Mannich‐type reaction of hydroxyketone using a Et2Zn/linked‐BINOL complex: Synthesis of either anti‐ or syn‐amino alcohols . J. Am. Chem. Soc. , 126 : 8777 – 8785 .
   PubMedGoogle Scholar
• Trost , B. M. and Yeh , V. S. C. 2002 . A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction . Angew. Chem. Int. Ed. , 41 : 861 – 863 .
   PubMed Web of Science ®Google Scholar
• Trost , B. M. and Mino , T. 2003 . Desymmetrization of meso 1,3‐ and 1,4‐diols with a dinuclear zinc asymmetric catalyst . J. Am. Chem. Soc. , 125 : 2410 – 2411 .
   PubMedGoogle Scholar
• Trost , B. M. and Terrell , M. L. R. 2003 . A direct catalytic asymmetric Mannich‐type reaction to syn‐amino alcohols . J. Am. Chem. Soc. , 125 : 338 – 339 .
   PubMed Web of Science ®Google Scholar
• Belokon , Y. N. , North , M. , Maleev , V. I. , Voskoboev , N. V. , Moskalenko , M. A. , Peregudov , A. S. , Dmitriev , A. V. , Ikonnikov , N. S. and Kagan , H. B. 2004 . Homogeneous catalysis: In situ formation of a heterobimetallic chiral [(salen)TiIV]/[(salen)VV] catalyst for the asymmetric addition of TMSCN to benzaldehyde . Angew. Chem. Int. Ed. , 43 : 4085 – 4089 .
   PubMedGoogle Scholar
• Kobayashi , S. , Arai , K. , Shimizu , H. , Ihori , Y. , Ishitani , H. and Yamashita , Y. 2005 . A novel dinuclear chiral niobium complex for Lewis acid catalyzed enantioselective reactions: Design of a tridentate ligand and elucidation of the catalyst structure . Angew. Chem. Int. Ed. , 44 : 761 – 764 .
   PubMedGoogle Scholar
• Yang , M. , Zhu , C. , Yuan , F. , Huang , Y. and Pan , Y. 2005 . Enantioselective ring‐opening reaction of meso‐epoxides with ArSeH catalyzed by heterometallic Ti‐Ga‐Salen system . Org. Lett. , 7 : 1927 – 1930 .
   PubMed Web of Science ®Google Scholar
• Gandelman , M. K. and Jacobsen , E. N. 2005 . Highly enantioselective catalytic conjugate addition of N‐heterocycles to a,b‐unsaturated ketones and imides . Angew. Chem. Int. Ed. , 44 : 2393 – 2397 .
   PubMedGoogle Scholar
• Tokunaga , M. , Larrow , J. F. , Kakiuchi , F. and Jacobsen , E. N. 1997 . Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis . Science , 277 : 936 – 938 .
   PubMed Web of Science ®Google Scholar
• Furrow , M. E. , Schaus , S. E. and Jacobsen , E. N. 1998 . Practical access to highly enantioenriched C‐3 building blocks via hydrolytic kinetic resolution . J. Org. Chem. , 63 : 6776 – 6777 .
   PubMed Web of Science ®Google Scholar
• Ready , J. M. and Jacobsen , E. N. 2002 . A practical oligomeric [(salen)Co] catalyst for asymmetric epoxide ring‐opening reactions . Angew. Chem. Int. Ed. , 41 : 1374 – 1377 .
   PubMedGoogle Scholar
• White , D. E. and Jacobsen , E. N. 2003 . New oligomeric catalyst for the hydrolytic kinetic resolution of terminal epoxides under solvent‐free conditions . Tetrahedron: Asymmetry , 14 : 3633 – 3638 .
   Web of Science ®Google Scholar
• Thakur , S. S. , Li , W. , Kim , S. J. and Kim , G.‐J. 2005 . Highly reactive and enantioselective kinetic resolution of terminal epoxides with H2O and HCl catalyzed by new chiral (salen)Co complex linked with Al . Tetrahedron Lett. , 46 : 2263 – 2266 .
   Web of Science ®Google Scholar
• Shin , C. K. , Kim , S. J. and Kim , G.‐J. 2004 . New chiral cobalt salen complexes containing Lewis acid BF3: A highly reactive and enantioselective catalyst for the hydrolytic kinetic resolution of epoxides . Tetrahedron Lett. , 45 : 7429 – 7433 .
   Web of Science ®Google Scholar
• Kim , G.‐J. , Lee , H. and Kim , S.‐J. 2003 . Catalytic activity and recyclability of new enantioselective chiral Co–salen complexes in the hydrolytic kinetic resolution of epichlorohydrine . Tetrahedron Lett. , 44 : 5005 – 5008 .
   Web of Science ®Google Scholar
• Thakur , S. S. , Li , W. , Shin , C. K. and Kim , G.‐J. 2005 . Enantioselective hydrolytic kinetic resolution of 1,2‐epoxy‐3‐phenoxy propane derivatives by new chiral (salen) cobalt complexes . Catal. Lett. , 104 : 151 – 156 .
   Google Scholar
• Kwon , M. and Kim , G.‐J. 2003 . Synthesis of polymeric salen complexes and application in the enantioselective hydrolytic kinetic resolution of epoxides as catalysts . Catal. Today , 87 : 145 – 151 .
   Web of Science ®Google Scholar
• Spencer , K. M. , Cianciosi , S. J. , Baldwin , J. E. , Freedman , T. B. and Nafie , L. A. 1990 . Appl. Spectros. , 44 : 235
   Google Scholar
• Freedman , T. B. , Cao , X. , Dukor , R. K. and Nafie , L. A. 2003 . Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism . Chirality , 15 : 743
   PubMed Web of Science ®Google Scholar
• Atwood , D. and Harvey , M. J. 2001 . Group 13 compounds incorporating salen ligands . Chem. Rev. , 101 : 37 – 52 . references cited therein
   PubMed Web of Science ®Google Scholar
• Atwood , D. and Wei , P. 1997 . An unusual imine (NC) alkylalumination reaction . Chem. Commun. , : 1427 – 1428 .
   Google Scholar
• Solari , E. , Corazza , F. , Floriani , C. , Chiesi‐Villa , A. and Guastini , C. 1990 . Polydentate ligand exchange via formation of a dimetallic complex: Crystal structures of [(thf)Fe(acen)MCl2](M=Fe or Zn), [ClFe(salphen)FeCl(thf)2], [Ti(acen)(thf)2][CoCl3(thf)], and [Ti(acen)(thf)2]2 [Fe3Cl8(thf)2][acenN,N‐ethylenebis(acetylacetoneiminate),salphen=N,N‐O‐phenylenebis(salicylideneiminate), and thf=tetrahydrofuran] . J. Chem. Soc., Dalton Trans. , : 1345 – 1355 .
   Google Scholar
• Gruber , S. J. , Harris , C. M. and Sinn , E. 1968 . Metal complexes as chelates, II: Binuclear complexes containing similar and dissimilar metal atoms . Inorg. Chem. , 2 : 268 – 273 .
   Web of Science ®Google Scholar
• Holm , R. H. , Everett , W. and Chakravorty , A. 1966 . Prog. Inorg. Chem. , 7 : 83 – 214 .
   Google Scholar
• Aoi , H. , Ishimori , M. and Tsuruta , T. 1975 . A study of the kinetic resolution of DL‐propylene oxide with optically active Co(I) (salen) type complexes . Bull. Chem. Soc. Jpn. , 48 : 1897 – 1901 .
   Google Scholar
• Huber , J. E. 1995 . Encyclopedia of Reagents for Organic Synthesis Edited by: Paquuette , L. A. Vol. 4 , 2326 New York : Wiley .
   Google Scholar
• Konsler , R. G. , Karl , J. and Jacobsen , E. N. 1998 . Cooperative asymmetric catalysis with dimeric salen complexes . J. Am. Chem. Soc. , 120 : 10780 – 10781 .
   Web of Science ®Google Scholar
• Breinbauer , R. and Jacobsen , E. N. 2000 . Cooperative asymmetric catalysis with dendrimeric [Co(salen)] complexes . Angew. Chem. Int. Ed. , 39 : 3604 – 3607 .
   PubMed Web of Science ®Google Scholar
• Yamamoto , H. 2000 . Lewis Acids in Organic Synthesis Vol. 1 and 2 , New York : Wiley .
   Google Scholar
• Kobayashi , S. , Busujima , T. and Nagayama , S. 2000 . A novel classification of Lewis acids on the basis of activity and selectivity . Chem.—Eur. J. , 6 : 3491 – 3494 . For examples using InCl3 and TlCl3 as Lewis acid see
   PubMed Web of Science ®Google Scholar
• Ranu , B. C. 2000 . Indium metal and its halides in organic synthesis . Eur. J. Org. Chem. , : 2347 – 2356 .
   Google Scholar
• Sengupta , S. and Mondal , S. 1999 . InCl3: A new Lewis acid catalyst for reactions with α‐diazocarbonyl compounds . Tetrahedron Lett. , 40 : 8685 – 8688 .
   Web of Science ®Google Scholar
• Uemura , S. , Sohma , K. and Okano , M. 1972 . Thallium(III) chloride tetrahydrate as a Lewis acid catalyst for aromatic alkylation and acylation . Bull. Chem. Soc. Jpn. , 45 : 860 – 863 .
   Google Scholar
• Nielson , L. P. C. , Stevenson , C. P. , Backmond , D. G. and Jacobsen , E. N. 2004 . Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides . J. Am. Chem. Soc. , 126 : 1360 – 1362 .
   PubMedGoogle Scholar
• Nicholas , B. , ElKoussi , A. , Kano , M. and Nakamura , T. 1988 . Improved delivery through biological membranes, 26: Design, synthesis, and pharmacological activity of a novel chemical delivery system for adrenergic blocking agents . J. Med. Chem. , 31 : 100 – 106 .
   PubMedGoogle Scholar