Reagent‐Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources

References

• Dowle , M. D. and Davies , D. I. 1979 . Synthesis and synthetic utility of halolactones . Chem. Soc. Rev. , 8 : 171 – 197 .
   Web of Science ®Google Scholar
• Cardillo , G. and Orena , M. 1990 . Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates . Tetrahedron , 46 : 3321 – 3408 . [CROSSREF]
   Web of Science ®Google Scholar
• Mulzer , J. 1991 . “ Halolactonization: the career of a reaction ” . In Organic Synthesis Highlights Edited by: Mulzer , J. , Altenbach , H. J. , Braun , M. , Krohn , K. and Reissig , H. U. 158 – 164 . Weinheim : VCH .
   Google Scholar
• Rousseau , G. and Robin , S. 1998 . Electrophilic cyclization of unsaturated amides . Tetrahedron , 54 : 13681 – 13736 . [CROSSREF]
   Web of Science ®Google Scholar
• Fuji , K. , Node , M. , Naniwa , Y. and Kawabata , T. 1990 . Enantioselective iodolactonization through diastereotopic group differentiation . Tetrahedron Lett. , 31 : 3175 – 3178 . [CROSSREF]
   Google Scholar
• Yokomatsu , T. , Iwasawa , H. and Shibuya , S. 1992 . Enantioselective halolactonisation of bis‐γ,δ‐unsaturated carboxylic acid derivatives: use of a sultam and oxazolidine‐2‐ones as chiral auxiliary . J. Chem. Soc., Chem. Commu. , : 728 – 729 . [CROSSREF]
   Google Scholar
• Moon , H. S. , Eisenberg , S. W.E. , Wilson , M. E. , Schore , N. E. and Kurth , M. J. 1994 . Preparation of nonracemic 3,5‐disubstituted‐γ‐butyrolactones: an effective sequent auxiliary for amide alkylation and iodolactonization . J. Org. Chem. , 59 : 6504 – 6505 .
   Google Scholar
• Moon , H. S. , Schore , N. E. and Kurth , M. J. 1994 . A polymer‐supported C2‐symmetric chiral auxiliary: preparation of non‐racemic 3,5‐disubstituted‐γ‐butyrolactones . Tetrahedron Lett. , 35 : 8915 – 8918 . [CROSSREF]
   Google Scholar
• Mckew , J. C. , Olmstead , M. M. and Kurth , M. J. 1994 . Doubly diastereoselective iodolactonizations: olefin and face selectivity in nona‐2,7‐diene‐5‐carboxylic acid cyclizations . J. Org. Chem. , 59 : 3389 – 3393 .
   Google Scholar
• Hoffmann , R. W. , Sturmer , R. and Harms , K. 1994 . A phenyl‐assisted asymmetric iodolactonization reaction . Tetrahedron Lett. , 35 : 6263 – 6266 . [CROSSREF]
   Google Scholar
• Kitagawa , O. , Momose , S. I. , Fushimi , Y. and Taguchi , T. 1999 . Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions . Tetrahedron Lett. , 40 : 8827 – 8831 . [CROSSREF]
   Web of Science ®Google Scholar
• Price , M. D. , Kurth , M. J. and Schore , N. E. 2002 . Comparison of solid‐phase and solution‐phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ‐butyrolactones . J. Org. Chem. , 67 : 7769 – 7773 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Fang , F. G. , Kishi , Y. , Matclich , M. C. and Scola , P. M. 1992 . Synthetic studies towards halichondrins: synthesis of the left halves of norhalichondrins and homohalichondrins . Tetrahedron Lett. , 33 : 1557 – 1560 . [CROSSREF]
   Google Scholar
• Shi , Y. , Peng , L. F. and Kishi , Y. 1997 . Enantioselective total synthesis of fumonisin B2 . J. Org. Chem. , 62 : 5666 – 5667 . [CROSSREF]
   Web of Science ®Google Scholar
• Cuzzupe , A. N. , Diflorio , R. and Rizzacasa , M. A. 2002 . Enantiospecific synthesis of the phospholipase A2 inhibitor (−)‐cinatrin . J. Org. Chem. , 67 : 4392 – 4398 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Kitagawa , O. , Hanano , T. , Tanabe , K. , Shiro , M. and Taguchi , T. 1992 . Enantioselective halocyclization reaction using a chiral titanium complex . J. Chem. Soc., Chem. Commu. , : 1005 – 1007 . [CROSSREF]
   Google Scholar
• Grossman , R. B. and Trupp , R. 1998 . The first reagent‐controlled asymmetric halolactonizations. Dihydroquinidine‐halogen complexes as chiral sources of positive halogen ion . J. Can J. Chem. , 76 : 1233 – 1237 . [CROSSREF]
   Google Scholar
• Haas , J. , Piguel , S. and Wirth , T. 2002 . Reagent‐controlled stereoselective iodolactonizations . Org. Lett. , 4 : 297 – 300 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Cui , X. L. and Brown , R. S. 2000 . Mechanistic evaluation of the halocyclization of 4‐penten‐1‐ol by some bis(2‐substituted pyridine) and bis(2,6‐disubstituted pyridine(bromium triflates . J. Org. Chem. , 65 : 5653 – 5658 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Richard , K. H. , Raghovan , S. and Seiji , S. 1972 . Asymmetric induction in the thermal reactions of allylic alcohols with N,N‐dimethylacetamide dimethylacetal and triethyl orthoacetate . J. Org. Chem. , 37 : 3737 – 3740 .
   Google Scholar