Critical perspective: Named reactions discovered and developed by women

Accounts of Chemical Research

Volumn 44, Issue 5, 2011, Pages 311-321

  Olson, Julie A ^a   Shea, Kevin M ^a  

^a SMITH COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79956207491     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar100114m     Document Type: Review

References (56)

1. For books on the subject, see: Li, J. J. Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, 4 th ed.; Springer-Verlag: Berlin, 2009.
2. Wang, Z. Comprehensive Organic Name Reactions and Reagents; Wiley: Hoboken, NJ, 2009.
3. Name Reactions for Homologations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009.
4. Name Reactions for Functional Group Transformations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007.
5. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms; Elsevier: Boston, 2005.
6. Morris, P. J. Named ReactionsForgotten Chemists Chem. Ind. 1999, 968-972
7. Drahl, C. In Names, History and Legacy Chem. Eng. News 2010, 88 (20) 31-33
8. Only Irma Goldberg, involved in two of the four reactions, is uniquely recognized for her contributions. The cases of Clare Hunsdiecker and Gertrude Maud Robinson are less clear since they shared the same surname as their husbands, Heinz Hunsdiecker and Sir Robert Robinson, respectively.
9. Evano, G.; Blanchard, N.; Toumi, M. Copper-Mediated Coupling Reactions and Their Applications in Natural Products and Designed Biomolecules Synthesis Chem. Rev. 2008, 108, 3054-3131
10. See ref 1b, Vol. 2, pp 1569 - 1575.
11. Creese, M. R. S. Ladies in the Laboratory II; Scarecrow Press: Lanham, MD; 2004, pp 184 - 185.
12. Goldberg, I. Phenylation with Presence of Copper as Catalyst Chem. Ber. 1906, 39, 1691-1692
13. Goldberg, I.; Nimerovsky, M. Triphenylamine and Triphenylaminecarboxylic Acid Chem. Ber. 1907, 40, 2448-2452
14. Goldberg, I. Phenylation of Primary Aromatic Amines Chem. Ber. 1908, 40, 4541-4546
15. See ref 1b, Vol. 2, pp 2217 - 2220.
16. Williams, T. I. Robert Robinson: Chemist Extraordinary; Oxford University Press: New York, 1990, and references therein.
17. He was awarded the Nobel Prize in 1947 for his interest in this work.
18. Robinson, G. M.; Robinson, R. A New Synthesis of Tetraphenylpyrrole J. Chem. Soc. 1918, 43, 639-645
19. It is fascinating to see the Robinsons explanation for this step in the mechanism nearly 50 years prior to the advent of modern thinking about pericyclic reactions.
20. See ref 1d, pp 623 - 629.
21. Jacques, J. In Regard to the Borodin-Hunsdiecker Reaction C. R. Acad. Sci. 1999, 2, 181-183
22. Hunsdiecker, H.; Hunsdiecker, C. Degradation of the Salts of Aliphatic Acids by Bromine Chem. Ber. 1942, 75B, 291-297
23. See ref 1c, Vol. 2, pp 293 - 304.
24. Jacques, J. Bianka Tchoubar (1910-1990) New J. Chem. 1992, 16, 11-18 and references therein.
25. Tchoubar, B. Extension of Alicyclic Rings of 1-(Aminomethyl)cycloalkanols by Nitrous Deamination. III. Theoretical Consideration of the Reaction Mechanism of Nitrous Deamination of Amino Alcohols Bull. Soc. Chim. 1949, 16, 169-172 and references therein
26. Murray, A. W. Molecular Rearrangements Org. React. Mech. 2003, 487-615
27. Cope joined the faculty at Bryn Mawr in 1934. He moved to Columbia in 1941 and to MIT in 1945.
28. Cope, A. C.; Hardy, E. M. The Introduction of Substituted Vinyl Groups. V. A Rearrangement Involving the Migration of an Allyl Group in a Three-Carbon System J. Am. Chem. Soc. 1940, 62, 441-444
29. Cope, A. C.; Hofmann, C. M.; Hardy, E. M. The Rearrangement of Allyl Groups in Three-Carbon Systems II J. Am. Chem. Soc. 1941, 63, 1852-1857
30. Woodward, R. B.; Hoffmann, R. Selection Rules for Sigmatropic Reactions J. Am. Chem. Soc. 1965, 87, 2511-2513
31. Castro, A. M. M. Claisen Rearrangement over the Past Nine Decades Chem. Rev. 2004, 104, 2939-3002
32. Wintner, C. E. Recollecting the Institute of Organic Chemistry, ETH Zurich, 1972-1990 Chimia 2006, 60, 142-148 (Pubitemid 43587055)
33. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Claisen Rearrangement of Allyl and Benzyl Alcohols by N, N -Dimethylacetamide Acetals Helv. Chim. Acta 1964, 47, 2425-2429
34. Felix, D.; Gschwend-Steen, K.; Wick, A. E.; Eschenmoser, A. Claisen Rearrangement of Allyl and Benzyl Alcohols with 1-Dimethylamino-1-methoxyethene Helv. Chim. Acta 1969, 52, 1030-1042
35. Constantieux, T.; Rodriguez, J. Synthesis by Fragmentation and Rearrangement. In Science of Synthesis; Cossy, J., Ed.; Thieme: New York, 2005; Vol. 26, pp 413 - 462.
36. Eschenmoster, A.; Felix, D.; Ohloff, G. New Fragmentation Reaction of α,β-Unsaturated Carbonyls. Synthesis of Exaltone and rac-Muscone from Cyclododecanone Helv. Chim. Acta 1967, 50, 708-713
37. Tanabe, M.; Crowe, D. R.; Dehn, R. L.; Detre, G. The Synthesis of Secosteroid Acetylenic Ketones Tetrahedron Lett. 1967, 8, 3739-3743
38. Felix, D.; Muller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. α,β-Epoxyketone to Alkynone Fragmentation II. Pyrolytic Decomposition of Hydrazones from α,β-Epoxyketones and N-Aminoaziridines Helv. Chim. Acta 1972, 55, 1276-1319 and references therein
39. See ref 1c, Vol. 1, pp 284 - 298.
40. Nicholas is currently a professor at Oklahoma University.
41. Lockwood, R. F.; Nicholas, K. M. Transition Metal-Stabilized Carbenium Ions as Synthetic Intermediates. I. α-[(Alkynyl)dicobalt hexacarbonyl] Carbenium Ions as Propargylating Agents Tetrahedron Lett. 1977, 4163-4166
42. See ref 1d, pp 545 - 550.
43. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. A Rapid Esterification by Mixed Anhydride and its Application to Large-Ring Lactonization Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993
44. See ref 1b, Vol. 3, pp 2435 - 2438.
45. Roush was at MIT from 1979-1987 and then moved to the University of Indiana. He is currently at the Scripps Research Institute in Jupiter, FL.
46. Roush, W. R.; Palkowitz, A. D.; Ando, K. Acyclic Diastereoselective Synthesis Using Tartrate Ester Modified Crotylboronates. Double Asymmetric Reactions with α-Methyl Chiral Aldehydes and Synthesis of the C(19)-C(29) Segment of Rifamycin S J. Am. Chem. Soc. 1990, 112, 6348-6359 and references therein (Pubitemid 20271850)
47. Palucki, M. Jacobsen-Katsuki Epoxidation. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005; pp 29 - 43.
48. Jacobsen was on the faculty at Illinois from 1988 to 1993 when he moved to his current position at Harvard.
49. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (Salen)manganese Complexes J. Am. Chem. Soc. 1990, 112, 2801-2803
50. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Catalytic Asymmetric Epoxidation of Unfunctionalized Olefins Using Chiral (Salen)manganese (III) Complexes Tetrahedron Asymm. 1991, 2, 481-494 and references therein
51. Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. Acyclic Stereocontrol Between Remote Atom Centers via Intramolecular and Intermolecular Stereo-communication Tetrahedron 2001, 57, 2917-2951 (Pubitemid 32322479)
52. Myers joined the faculty at Caltech in 1986 and moved to his current position at Harvard in 1998.
53. Myers, A. G.; McKinstry, L. Practical Syntheses of Enantiomerically Enriched ?-Lactones and ?-Hydroxy Ketones by Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives J. Org. Chem. 1996, 61, 2428-2440 and references therein (Pubitemid 26139832)
54. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. Pseudoephedrine as a Practical Chiral Auxiliary for the Synthesis of Highly Enantiomerically Enriched Carboxylic Acids, Alcohols, Aldehydes, and Ketones J. Am. Chem. Soc. 1997, 119, 6496-6511 (Pubitemid 27322328)
55. Heine Reaction: Mary Emma Fetter, Elva Mae Nicholson, Eleanor M. Johnson, Dorothy C. King. Midland Alpine Borane Reduction: Sue Greer, Deborah C. McDowell. Minisci Reaction: Mirella Cecere, Rosanna Bernardi. Regitz Diazo Transfer: Annemarie Liedhegener. Shapiro Reaction: Marsha J. Heath. Stille-Kelly Coupling: Vidya Bhushan. [1,2]- and [2,3]-Wittig Rearrangement: Lisa Lohmann.
56. Raber, L. R. Women Now 17% of Chemistry Faculty Chem. Eng. News 2010, 88 (9) 42-43 and references therein