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Volumn 62, Issue 6, 1997, Pages 1702-1712

Single Stereodifferentiation Associated with Carbon Atom Insertion during the Oxonium Ion-Initiated Pinacol Rearrangement of Dihydrofuranyl and Dihydropyranyl Carbinols

(3) Paquette, Leo A a Lanter, James C a Johnston, Jeffrey N a

a OHIO STATE UNIVERSITY (United States)

Author keywords

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Indexed keywords

EID: 0000365337 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo962019j Document Type: Article

Times cited : (53)

References (63)

1
- 0003869642
- Marcel Dekker: New York
- Reviews: (a) Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (d) Koert, U. Synthesis 1995, 115. (d) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1982) Polyether Antibiotics
- Westley, J.W.¹

2
- 0003905731
- Morrison, J. D., Ed.; Academic Press: New York
- Reviews: (a) Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (d) Koert, U. Synthesis 1995, 115. (d) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1984) Asymmetric Synthesis , vol.3
- Bartlett, P.A.¹

3
- 15844366864
- Reviews: (a) Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (d) Koert, U. Synthesis 1995, 115. (d) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1987) Tetrahedron , vol.43 , pp. 3309
- Boivin, T.L.B.¹

4
- 0028812058
- Reviews: (a) Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (d) Koert, U. Synthesis 1995, 115. (d) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1995) Synthesis , pp. 115
- Koert, U.¹

5
- 0027200955
- Reviews: (a) Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982. (b) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309. (d) Koert, U. Synthesis 1995, 115. (d) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1711
- Harmange, J.-C.¹ Figadère, B.²

6
- 0026488490
- (a) Li, G.; Still, W. C. Tetrahedron Lett. 1992, 33, 5929.
- (1992) Tetrahedron Lett. , vol.33 , pp. 5929
- Li, G.¹ Still, W.C.²

7
- 0001767306
- (b) Li, G.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 3804.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3804
- Li, G.¹ Still, W.C.²

8
- 0001588615
- (c) Armstrong, A.; Still, W. C. J. Org. Chem. 1992, 57, 4580.
- (1992) J. Org. Chem. , vol.57 , pp. 4580
- Armstrong, A.¹ Still, W.C.²

9
- 0000182192
- (d) Wang, X.; Erickson, S. D.; Iimori, T.; Still, W. C. J. Am. Chem. Soc. 1992, 114, 4128.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4128
- Wang, X.¹ Erickson, S.D.² Iimori, T.³ Still, W.C.⁴

10
- 0024803952
- (e) Iimori, T.; Erickson, S. D.; Rheingold, A. L.; Still, W. C. Tetrahedron Lett. 1989, 30, 6947.
- (1989) Tetrahedron Lett. , vol.30 , pp. 6947
- Iimori, T.¹ Erickson, S.D.² Rheingold, A.L.³ Still, W.C.⁴

11
- 0028007798
- (f) Burger, M. T.; Armstrong, A.; Guarnieri, F.; McDonald, D. Q.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 3593.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3593
- Burger, M.T.¹ Armstrong, A.² Guarnieri, F.³ McDonald, D.Q.⁴ Still, W.C.⁵

12
- 0027450635
- (a) Koert, U.; Stein, M.; Harms, K. Tetrahedron Lett. 1993, 34, 2299.
- (1993) Tetrahedron Lett. , vol.34 , pp. 2299
- Koert, U.¹ Stein, M.² Harms, K.³

13
- 33748231608
- (b) Koert, U.; Stein, M.; Harms, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1180.
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1180
- Koert, U.¹ Stein, M.² Harms, K.³

14
- 84985650846
- (c) Koert, U.; Wagner, H.; Pidun, U. Chem. Ber. 1994, 127, 1447.
- (1994) Chem. Ber. , vol.127 , pp. 1447
- Koert, U.¹ Wagner, H.² Pidun, U.³

15
- 0001712252
- (d) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5354
- Hopkins, M.H.¹ Overman, L.E.² Rishton, G.M.³

16
- 0000773305
- (e) Brown, M. J.; Harrison, T.; Herrinton, P. M.; Hopkins, M. H.; Hutchinson, K. D.; Mishra, P.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5365.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5365
- Brown, M.J.¹ Harrison, T.² Herrinton, P.M.³ Hopkins, M.H.⁴ Hutchinson, K.D.⁵ Mishra, P.⁶ Overman, L.E.⁷

17
- 0029922072
- (a) Paquette, L. A.; Branan, B. M.; Stepanian, M. Tetrahedron Lett. 1996, 37, 1721.
- (1996) Tetrahedron Lett. , vol.37 , pp. 1721
- Paquette, L.A.¹ Branan, B.M.² Stepanian, M.³

18
- 17544369765
- (b) Paquette, L. A.; Stepanian, M.; Branan, B. M.; Edmondson, S. D.; Bauer, C. B.; Rogers, R. D. J. Am. Chem. Soc. 1996, 118, 4504.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 4504
- Paquette, L.A.¹ Stepanian, M.² Branan, B.M.³ Edmondson, S.D.⁴ Bauer, C.B.⁵ Rogers, R.D.⁶

19
- 1542713457
- (c) Paquette, L. A.; Lowinger, T. B.; Bolin, D. G.; Branan, B. M. J. Org. Chem. 1996, 61, 7482.
- (1996) J. Org. Chem. , vol.61 , pp. 7482
- Paquette, L.A.¹ Lowinger, T.B.² Bolin, D.G.³ Branan, B.M.⁴

20
- 0000991382
- (d) Paquette, L. A.; Stepanian, M.; Mallavadhani, U. V.; Cutarelli, T. D.; Lowinger, T. B.; Klemeyer, H. J. Org. Chem. 1996, 61, 7492.
- (1996) J. Org. Chem. , vol.61 , pp. 7492
- Paquette, L.A.¹ Stepanian, M.² Mallavadhani, U.V.³ Cutarelli, T.D.⁴ Lowinger, T.B.⁵ Klemeyer, H.⁶

21
- 17444401848
- (a) Boeckman, R. K., Jr.; Bruza, K. J. Tetrahedron 1981, 37, 3997.
- (1981) Tetrahedron , vol.37 , pp. 3997
- Boeckman Jr., R.K.¹ Bruza, K.J.²

22
- 49349136562
- (b) Boeckman, R. K., Jr.; Bruza, K. J. Tetrahedron Lett. 1977, 4187.
- (1977) Tetrahedron Lett. , pp. 4187
- Boeckman Jr., R.K.¹ Bruza, K.J.²

23
- 0000103701
- Paquette, L. A.; Lawhorn, D. E.; Teleha, C. A. Heterocycles 1990, 30, 765.
- (1990) Heterocycles , vol.30 , pp. 765
- Paquette, L.A.¹ Lawhorn, D.E.² Teleha, C.A.³

24
- 1542398790
- de Mayo, P., Ed.; Interscience Publishers: New York; Chapter 1
- (a) Pocker, Y. In Molecular Rearrangements, Part One; de Mayo, P., Ed.; Interscience Publishers: New York, 1963; Chapter 1.
- (1963) Molecular Rearrangements, Part One
- Pocker, Y.¹

25
- 1542713455
- de Mayo, P., Ed.; Interscience Publishers: New York; Chapter 3
- (b) Berson, J. A. In Molecular Rearrangements, Part One; de Mayo, P., Ed.; Interscience Publishers: New York, 1963; Chapter 3.
- (1963) Molecular Rearrangements, Part One
- Berson, J.A.¹

26
- 0001398419
- (a) Negri, J. T.; Rogers, R. D.; Paquette, L. A. J. Am. Chem. Soc. 1991, 113, 5073.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 5073
- Negri, J.T.¹ Rogers, R.D.² Paquette, L.A.³

27
- 33751391024
- (b) Paquette, L. A.; Negri, J. T.; Rogers, R. D. J. Org. Chem. 1992, 57, 3947.
- (1992) J. Org. Chem. , vol.57 , pp. 3947
- Paquette, L.A.¹ Negri, J.T.² Rogers, R.D.³

28
- 0000988001
- Paquette, L. A.; Andrews, J. F. P.; Vanucci, C.; Lawhorn, D. E.; Negri, J. T.; Rogers, R. D. J. Org. Chem. 1992, 57, 3956.
- (1992) J. Org. Chem. , vol.57 , pp. 3956
- Paquette, L.A.¹ Andrews, J.F.P.² Vanucci, C.³ Lawhorn, D.E.⁴ Negri, J.T.⁵ Rogers, R.D.⁶

29
- 0028861043
- (a) Lord, M. D.; Negri, J. T.; Paquette, L. A. J. Org. Chem. 1995, 60, 191.
- (1995) J. Org. Chem. , vol.60 , pp. 191
- Lord, M.D.¹ Negri, J.T.² Paquette, L.A.³

30
- 0027236101
- (b) Paquette, L. A.; Lord, M. D.; Negri, J. T. Tetrahedron Lett. 1993, 34, 5693 .
- (1993) Tetrahedron Lett. , vol.34 , pp. 5693
- Paquette, L.A.¹ Lord, M.D.² Negri, J.T.³

31
- 0029160607
- (a) Paquette, L. A.; Wang, H.-L. Tetrahedron Lett. 1995, 36, 6005.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6005
- Paquette, L.A.¹ Wang, H.-L.²

32
- 0000254625
- (b) Paquette, L. A.; Wang, H.-L. J. Org. Chem. 1996, 61, 1119.
- (1996) J. Org. Chem. , vol.61 , pp. 1119
- Paquette, L.A.¹ Wang, H.-L.²

33
- 0003942864
- John Wiley and Sons, Inc.: New York
- Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley and Sons, Inc.: New York, 1994.
- (1994) Stereochemistry of Organic Compounds
- Eliel, E.L.¹ Wilen, S.H.² Mander, L.N.³

34
- 0021775497
- Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
- (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 1
- Masamune, S.¹ Choy, W.² Petersen, J.S.³ Sita, L.R.⁴

35
- 0000101367
- For the use of this term in aldol chemistry, see (a) Heathcock, C. H.; Pirrung, M. G.; Buse, C. T.; Hagen, J. P.; Young, S. D.; Sohn, J. E. J. Am. Chem. Soc. 1979, 101, 7077. (b) Heathcock, C. H.; Pirrung, M. C.; Lampe, J.; Buse, C. T.; Young, S. D. J. Org. Chem. 1981, 46, 2290.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 7077
- Heathcock, C.H.¹ Pirrung, M.G.² Buse, C.T.³ Hagen, J.P.⁴ Young, S.D.⁵ Sohn, J.E.⁶

36
- 33845557437
- For the use of this term in aldol chemistry, see (a) Heathcock, C. H.; Pirrung, M. G.; Buse, C. T.; Hagen, J. P.; Young, S. D.; Sohn, J. E. J. Am. Chem. Soc. 1979, 101, 7077. (b) Heathcock, C. H.; Pirrung, M. C.; Lampe, J.; Buse, C. T.; Young, S. D. J. Org. Chem. 1981, 46, 2290.
- (1981) J. Org. Chem. , vol.46 , pp. 2290
- Heathcock, C.H.¹ Pirrung, M.C.² Lampe, J.³ Buse, C.T.⁴ Young, S.D.⁵

37
- 0042535912
- Goldsmith, D. J.; Liotta, D. C.; Volmer, M.; Hoekstra, W.; Waykole, L. Tetrahedron 1985, 41, 4873.
- (1985) Tetrahedron , vol.41 , pp. 4873
- Goldsmith, D.J.¹ Liotta, D.C.² Volmer, M.³ Hoekstra, W.⁴ Waykole, L.⁵

38
- 0000475159
- Ducoux, J. P.; Le Ménez, P.; Kunesch, N.; Wenkert, E. J. Org. Chem. 1993, 58, 1290.
- (1993) J. Org. Chem. , vol.58 , pp. 1290
- Ducoux, J.P.¹ Le Ménez, P.² Kunesch, N.³ Wenkert, E.⁴

39
- 0000254625
- Paquette, L. A.; Lanter, J. C.; Wang, H.-L. J. Org. Chem. 1996, 61, 1119.
- (1996) J. Org. Chem. , vol.61 , pp. 1119
- Paquette, L.A.¹ Lanter, J.C.² Wang, H.-L.³

40
- 0001548708
- Byström, S.; Högberg, H.-E.; Norin, T. Tetrahedron 1981, 37, 2249.
- (1981) Tetrahedron , vol.37 , pp. 2249
- Byström, S.¹ Högberg, H.-E.² Norin, T.³

41
- 0642298432
- and references therein
- Paquette, L. A.; Oplinger, J. A. Tetrahedron 1989, 45, 107 and references therein.
- (1989) Tetrahedron , vol.45 , pp. 107
- Paquette, L.A.¹ Oplinger, J.A.²

42
- 37049075715
- Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926.
- (1986) J. Chem. Soc., Chem. Commun. , pp. 926
- Hanessian, S.¹ Martin, M.² Desai, R.C.³

43
- 0000021944
- (a) Friesen, R. W.; Loo, R. W. J. Org. Chem. 1991, 56, 4821.
- (1991) J. Org. Chem. , vol.56 , pp. 4821
- Friesen, R.W.¹ Loo, R.W.²

44
- 0001438541
- (b) Friesen, R. W.; Sturino, C. F.; Daljeet, A. K.; Kolaczewska, A. J. Org. Chem. 1991, 56, 1944.
- (1991) J. Org. Chem. , vol.56 , pp. 1944
- Friesen, R.W.¹ Sturino, C.F.² Daljeet, A.K.³ Kolaczewska, A.⁴

45
- 0011674952
- Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinaÿ, P. Tetrahedron Lett. 1986, 27, 6201.
- (1986) Tetrahedron Lett. , vol.27 , pp. 6201
- Lesimple, P.¹ Beau, J.-M.² Jaurand, G.³ Sinaÿ, P.⁴

46
- 0000405792
- Schmidt, R. R.; Preuss, R.; Betz, R. Tetrahedron Lett. 1987, 28, 6591.
- (1987) Tetrahedron Lett. , vol.28 , pp. 6591
- Schmidt, R.R.¹ Preuss, R.² Betz, R.³

47
- 85033536123
- Barber, C.; Jarowicki, K.; Kocienski, P. Synlett 1991, 197.
- (1991) Synlett , pp. 197
- Barber, C.¹ Jarowicki, K.² Kocienski, P.³

48
- 0002899916
- Wulff, W. D.; Peterson, G. A.; Bauta, W. E.; Chan, K.-S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277.
- (1986) J. Org. Chem. , vol.51 , pp. 277
- Wulff, W.D.¹ Peterson, G.A.² Bauta, W.E.³ Chan, K.-S.⁴ Faron, K.L.⁵ Gilbertson, S.R.⁶ Kaesler, R.W.⁷ Yang, D.C.⁸ Murray, C.K.⁹

49
- 0025336659
- (a) Jarowicki, K.; Kocienski, P.; Marczak, S.; Willson, T. Tetrahedron Lett. 1990, 31, 3433.
- (1990) Tetrahedron Lett. , vol.31 , pp. 3433
- Jarowicki, K.¹ Kocienski, P.² Marczak, S.³ Willson, T.⁴

50
- 0026344608
- (b) Kocienski, P.; Jarowicki, K.; Marczak, S. Synthesis 1991, 1191.
- (1991) Synthesis , pp. 1191
- Kocienski, P.¹ Jarowicki, K.² Marczak, S.³

51
- 0028880344
- Downham, R.; Edwards, P. J.; Entwistle, D. A.; Hughes, A. B.; Kim, K. S.; Ley, S. V. Tetrahedron: Asymmetry 1995, 6, 2403.
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2403
- Downham, R.¹ Edwards, P.J.² Entwistle, D.A.³ Hughes, A.B.⁴ Kim, K.S.⁵ Ley, S.V.⁶

52
- 0028657561
- Genicot, C.; Ley, S. V. Synthesis 1994, 1275.
- (1994) Synthesis , pp. 1275
- Genicot, C.¹ Ley, S.V.²

53
- 1542503833
- Wiley: New York; Coll.
- (a) Smith, N. R.; Wiley, R. H. Organic Syntheses; Wiley: New York, 1963; Coll. Vol. IV, p 549.
- (1963) Organic Syntheses , vol.4 , pp. 549
- Smith, N.R.¹ Wiley, R.H.²

54
- 0006158805
- Wiley: New York; Coll.
- (b) Smith, N. R.; Wiley, R. H. Organic Syntheses; Wiley: New York, 1963; Coll. Vol. IV, p 337.
- (1963) Organic Syntheses , vol.4 , pp. 337
- Smith, N.R.¹ Wiley, R.H.²

55
- 0001381021
- McKelvey, K. D.; Kawada, Y.; Sugawara, T.; Iwamura, H. J. Org. Chem. 1981, 46, 4948.
- (1981) J. Org. Chem. , vol.46 , pp. 4948
- McKelvey, K.D.¹ Kawada, Y.² Sugawara, T.³ Iwamura, H.⁴

56
- 37049109502
- Kocienski, P.; Yeates, C. J. Chem. Soc., Perkin Trans. 1 1985, 1879.
- (1985) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1879
- Kocienski, P.¹ Yeates, C.²

57
- 84987358468
- (e) Rosenberger, M.; Andrews, D.; DiMaria, F.; Duggan, A. J.; Saucy, G. Helv. Chim. Acta 1972, 55, 249.
- (1972) Helv. Chim. Acta , vol.55 , pp. 249
- Rosenberger, M.¹ Andrews, D.² Dimaria, F.³ Duggan, A.J.⁴ Saucy, G.⁵

58
- 0000774684
- Ley, S. V.; Lygo, B.; Sternfeld, F.; Wonnacott, A. Tetrahedron 1986, 42, 4333.
- (1986) Tetrahedron , vol.42 , pp. 4333
- Ley, S.V.¹ Lygo, B.² Sternfeld, F.³ Wonnacott, A.⁴

59
- 0003536850
- Pergamon Press: Oxford, England; Chapter 2
- Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, England, 1983; Chapter 2.
- (1983) Stereoelectronic Effects in Organic Chemistry
- Deslongchamps, P.¹

60
- 0001065201
- Paquette, L. A.; Tae, J. J. Org. Chem. 1996, 61, 7860.
- (1996) J. Org. Chem. , vol.61 , pp. 7860
- Paquette, L.A.¹ Tae, J.²

61
- 0030894227
- (a) Paquette, L. A.; Kinney, M. J.; Dullweber, U. J. Org. Chem. 1997, 62, 1713.
- (1997) J. Org. Chem. , vol.62 , pp. 1713
- Paquette, L.A.¹ Kinney, M.J.² Dullweber, U.³

62
- 0027141343
- (b) Paquette, L. A.; Dullweber, U.; Cowgill, L. D. Tetrahedron Lett. 1993, 34, 8019.
- (1993) Tetrahedron Lett. , vol.34 , pp. 8019
- Paquette, L.A.¹ Dullweber, U.² Cowgill, L.D.³

63
- 85033157790
- note
- Crystallographic experimental details, bond lengths, bond lengths involving the hydrogen atoms, bond angles, positional parameters and B(eq) values, anisotropic displacement parameters, and positional parameters for the hydrogen atoms for 28-2,4-DNP, 31-2,4-DNP, 34-2,4-DNP, and 48-2,4-DNP have been deposited with the Cambridge Crystallographic Data Centre. These data can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.

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