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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 19
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Original Articles

Dianion-Based Methodology for the Preparation of 2,3-Disubstitutrd Butyrolactones

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Pages 3371-3378 | Received 03 Jul 1989, Published online: 24 Oct 2006

References

  • Augustine , R. L. , ed. 1979 . Carbon-Carbon Bond Formation , Vol. 1 , New York : Marcel Dekker, Inc. .
  • House , H. O. 1972 . Modern Synthetic Reactions , 2nd Ed. Edited by: Benjamin , W. A. Menlo Park, CA
  • Belletire , J. L. , Spletzer , E. G. and Pinhas , A. R. 1984 . Tetrahedron Lett. , 25 : 5969
  • Belletire , J. L. and Fremont , S. L. 1986 . Tetrahedron Lett. , 27 : 127
  • Belletire , J. L. and Fry , D. F. 1987 . J. Org. Chem. , 52 : 2549
  • Belletire , J. L. and Fry , D. F. 1988 . J. Org. Chem. , 53 : 4724
  • Belletire , J. L. , Fremont , S. L. and Fry , D. F. 1988 . Synth. Commun. , 18 : 699
  • Belletire , J. L. and Spletzer , E. G. 1986 . Tetrahedron Lett. , 27 : 131
  • Belletire , J. L. and Fry , D. F. 1988 . Synth. Commun. , 18 : 29 Of interest, over-reduction, normally an undesired side reaction, can be combined with Type I dianion coupling and a traditional sulfonamide cleavage procedure to provide an efficient route to 2,3-disubstituted-1,4-diamines. Such diamines have value as complex ligands.
  • Belletire , J. L. and Fry , D. F. 1988 . University of Cincinnati . All the observed increases were the result of delicate modification of the reaction conditions such as using diethyl ether as a co-solvent (an approximately 6:1 diethyl ether/THF mixture was best) plus very careful control of the borane reduction temperature. unpublished results, manuscript in preparation
  • Belletire , J. L. and Mahmoodi , N. O. University of Cincinnati . This study was in connection with successful experiments involving the use of tin hydride/AIBN mixtures as methodology for the cyclization of alpha-bromo esters prepared from substituted cinnamyl alcohols. This cyclization produced lignans (including a straightforward synthesis of 8 (as a diastereoisomeric mixture) whose spectra and chromatographic behavior were compared with 8 synthesized by the above dianion coupling approach) as well as a promising model study (involving the independent preparation of 12d) via tin hydride/AlBN (spectra identical to 12d from the dianion coupling sequence) for the anti-glaucoma butyrolactone alkaloid pilocarpine. unpublished results, manuscript submitted
  • Asano , Y. , Kamikawa , T. and Tokoroyama , T. 1976 . Bull. Chem., Soc. Jpn. , 49 : 3232
  • Damon , R. E. , Schlessinger , R. H. and Blount , J. F. 1976 . J. Org. Chem. , 41 : 3773
  • Huynh , C. , Derguini Boumechal , D. and Linstrummell , G. 1976 . Tetrahedron Lett. , 20 : 1503
  • Katzenellenbogen , J. A. and Crumine , A. L. 1976 . J. Am. Chem. Soc. , 98 : 4925

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