SCOPUS 정보 검색 플랫폼

Volumn 67, Issue 25, 2002, Pages 8744-8752

Connective synthesis of polysubstituted tetrahydropyrans by a novel and stereocontrolled metallo-ene/Intramolecular Sakurai Cyclization sequence

(2) Leroy, Bernard a Markó, István E a

a UNIVERSITÉ CATHOLIQUE DE LOUVAIN (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLMETALATION;

DERIVATIVES; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037073938 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo025899c Document Type: Article

Times cited : (48)

References (46)

1
- 1542502091
- (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
- (1993) Chem. Rev. , vol.93 , pp. 1897
- Yasumoto, T.¹ Murata, M.²

2
- 0001377493
- (b) Shimizu, Y. Chem. Rev. 1993, 93, 1685.
- (1993) Chem. Rev. , vol.93 , pp. 1685
- Shimizu, Y.¹

3
- 0001021862
- (a) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753.
- (1993) Chem. Rev. , vol.93 , pp. 1753
- Kobayashi, J.¹ Ishibashi, M.²

4
- 0028814874
- (b) Bauer, I.; Maranda, L.; Young, K. A.; Shimizu, Y.; Huang, S. Tetrahedron Lett 1995, 36, 991.
- (1995) Tetrahedron Lett. , vol.36 , pp. 991
- Bauer, I.¹ Maranda, L.² Young, K.A.³ Shimizu, Y.⁴ Huang, S.⁵

5
- 0028067799
- (c) Kobayashi, J.; Yamagushi, N.; Ishibashi, M. Tetrahedron Lett. 1994, 35, 7049.
- (1994) Tetrahedron Lett. , vol.35 , pp. 7049
- Kobayashi, J.¹ Yamagushi, N.² Ishibashi, M.³

6
- 0026322293
- Satake, M.; Murata, M.; Yasumoto, T.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 1991, 113, 9859.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 9859
- Satake, M.¹ Murata, M.² Yasumoto, T.³ Fujita, T.⁴ Naoki, H.⁵

7
- 0029153948
- (a) Paul, G. K.; Matsumori, N.; Murata, M.; Tachibana, K. Tetrahedron Lett. 1995, 36, 6279.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6279
- Paul, G.K.¹ Matsumori, N.² Murata, M.³ Tachibana, K.⁴

8
- 0001569209
- (b) Paul, G. K.; Matsumori, M.; Konoki, K.; Murata, M.; Tachibana, K. J. Mar. Biotechnol. 1997, 5, 124.
- (1997) J. Mar. Biotechnol. , vol.5 , pp. 124
- Paul, G.K.¹ Matsumori, M.² Konoki, K.³ Murata, M.⁴ Tachibana, K.⁵

9
- 0033518615
- Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 870
- Murata, M.¹ Matsuoka, S.² Matsumori, N.³ Paul, G.K.⁴ Tachibana, K.⁵

10
- 15844366864
- (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
- (1987) Tetrahedron , vol.43 , pp. 3309
- Boivin, T.L.B.¹

11
- 0034616466
- and references therein
- (b) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291 and references therein.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1291
- Elliott, M.C.¹

12
- 0027436079
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1993) Tetrahedron Lett. , vol.34 , pp. 6595
- Markó, I.E.¹ Bayston, D.J.²

13
- 0033538663
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1999) Tetrahedron Lett. , vol.40 , pp. 5259
- Markó, I.E.¹ Plancher, J.-M.²

14
- 1542800220
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1968) Acc. Chem. Res. , vol.1 , pp. 1
- Johnson, W.S.¹

15
- 37049107437
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1984) J. Chem. Soc., Perkin Trans. 1 , pp. 1815
- Chow, H.-F.¹ Fleming, I.²

16
- 0023845889
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1988) J. Org. Chem. , vol.53 , pp. 911
- Coppi, L.¹ Ricci, A.² Taddei, M.³

17
- 0024841749
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1989) J. Org. Chem. , vol.54 , pp. 5768
- Wei, Z.Y.¹ Wang, D.² Li, J.S.³ Chan, T.H.⁴

18
- 0028948102
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1995) Tetrahedron Lett. , vol.36 , pp. 2453
- Mohr, P.¹

19
- 0001207667
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1997) J. Org. Chem. , vol.62 , pp. 3426
- Semeyn, C.¹ Blaauw, R.H.² Hiemstra, H.³ Speckamp, W.N.⁴

20
- 0000714850
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1998) J. Org. Chem. , vol.63 , pp. 6096
- Suginome, M.¹ Iwanami, T.² Ito, Y.³

21
- 0033605402
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1999) Tetrahedron Lett. , vol.40 , pp. 1627
- Yang, J.¹ Viswanathan, G.S.² Li, C.J.³

22
- 0001309251
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1999) Org. Lett. , vol.1 , pp. 993
- Viswanathan, G.S.¹ Yang, J.² Li, C.-J.³

23
- 0035180198
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (2001) Tetrahedron Lett. , vol.42 , pp. 89
- Yadav, J.S.¹ Subba Reddy, B.V.² Mahesh Kumar, G.³ Murthy, C.V.S.R.⁴

24
- 0001154569
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1992) J. Org. Chem. , vol.57 , pp. 2211
- Markó, I.E.¹ Mekhalfia, A.² Bayston, D.J.³ Adams, H.⁴

25
- 0029921283
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1996) Synthesis , pp. 297
- Markó, I.E.¹ Bayston, D.J.²

26
- 0030914060
- (a) Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595. (b) Markó, I. E.; Plancher, J.-M. Tetrahedron Lett. 1999, 40, 5259. For similar strategies based upon the capture of an oxonium cation intermediate by allyl- or vinylsilanes, see: (a) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (b) Chow, H.-F.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1984, 1815. (c) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 911. (d) Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768. (e) Mohr, P. Tetrahedron Lett. 1995, 36, 2453. (f) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426. (g) Suginome, M.; Iwanami, T.; Ito, Y. J. Org. Chem. 1998, 63, 6096. (h) Yang, J.; Viswanathan, G. S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627. (i) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993. (j) Yadav, J. S.; Subba Reddy, B. V.; Mahesh Kumar, G.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89. (k) Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. (l) Markó, I. E.; Bayston, D. J; Synthesis 1996, 297. (m) Markó, I. E.; Chellé, F. Tetrahedron Lett. 1997, 38, 2895.
- (1997) Tetrahedron Lett. , vol.38 , pp. 2895
- Markó, I.E.¹ Chellé, F.²

27
- 0001797385
- Heteroatom-stabilized allylic anions
- Trost, B. M.; Fleming, I., Eds; Pergamon Press: Oxford, UK
- For excellent reviews on allylmetal species bearing α-alkoxy substituents, see: (a) Yamamoto, Y. Heteroatom-stabilized allylic anions. In Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991; Vol. 2, p 55. (b) Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665.
- (1991) Comprehensive Organic Synthesis , vol.2 , pp. 55
- Yamamoto, Y.¹

28
- 0033101277
- For excellent reviews on allylmetal species bearing α-alkoxy substituents, see: (a) Yamamoto, Y. Heteroatom-stabilized allylic anions. In Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991; Vol. 2, p 55. (b) Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665.
- (1999) Chem. Rev. , vol.99 , pp. 665
- Katritzky, A.R.¹ Piffl, M.² Lang, H.³ Anders, E.⁴

29
- 0034601643
- Some results have been previously reported in a communication: Markó, I. E.; Leroy, B. Tetrahedron Lett. 2000, 41, 7225.
- (2000) Tetrahedron Lett. , vol.41 , pp. 7225
- Markó, I.E.¹ Leroy, B.²

30
- 84985557593
- (a) Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, A. Angew. Chem., Int. Ed. Engl. 1981, 20, 1024.
- (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 1024
- Hoppe, D.¹ Hanko, R.² Brönneke, A.³ Lichtenberg, A.⁴

31
- 0021558291
- (b) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
- (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 932
- Hoppe, D.¹

32
- 84985580890
- (c) Hoppe, D.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 160.
- (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 160
- Hoppe, D.¹ Krämer, T.²

33
- 0026718563
- (d) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
- (1992) Tetrahedron , vol.48 , pp. 5657
- Zschage, O.¹ Hoppe, D.²

34
- 0030040452
- (e) Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
- (1996) Synthesis , pp. 141
- Paulsen, H.¹ Graeve, C.² Hoppe, D.³

35
- 0000129326
- (f) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283.
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2283
- Hoppe, D.¹ Hense, T.²

36
- 0002907091
- Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.
- (1984) Org. Synth. , vol.62 , pp. 58
- Trost, B.M.¹ Chan, D.M.T.² Nanninga, T.N.³

37
- 0012186825
- For the effect of oxygenated substituents on stereoselectivity in allyltitanation of aldehydes, see: Martin, S. F.; Li, W. J. Org. Chem. 1989, 54, 6129.
- (1989) J. Org. Chem. , vol.54 , pp. 6129
- Martin, S.F.¹ Li, W.²

38
- 0035803019
- Similar results have been obtained in our attempts to condense homoallylic alcohols such as 2 with α-hydroxyaldehydes or α,β-dihydroxyaldehydes. In these cases, however, degradation is observed instead of the Sakurai addition product. A modified strategy, based upon the use of allylstannane derivatives, allows the introduction of such aldehydes: (a) Leroy, B.; Markó, I. E. Tetrahedron Lett. 2001, 42, 8685. (b) Leroy, B.; Markó, I. E. Org. Lett. 2002, 4, 47.
- (2001) Tetrahedron Lett. , vol.42 , pp. 8685
- Leroy, B.¹ Markó, I.E.²

39
- 0037050523
- Similar results have been obtained in our attempts to condense homoallylic alcohols such as 2 with α-hydroxyaldehydes or α,β-dihydroxyaldehydes. In these cases, however, degradation is observed instead of the Sakurai addition product. A modified strategy, based upon the use of allylstannane derivatives, allows the introduction of such aldehydes: (a) Leroy, B.; Markó, I. E. Tetrahedron Lett. 2001, 42, 8685. (b) Leroy, B.; Markó, I. E. Org. Lett. 2002, 4, 47.
- (2002) Org. Lett. , vol.4 , pp. 47
- Leroy, B.¹ Markó, I.E.²

40
- 0029936615
- Gung, B. W. Tetrahedron 1996, 52, 5263.
- (1996) Tetrahedron , vol.52 , pp. 5263
- Gung, B.W.¹

41
- 33845278128
- Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 3588
- Maruoka, K.¹ Itoh, T.² Sakurai, M.³ Nonoshita, K.⁴ Yamamoto, H.⁵

42
- 0035932051
- For interactions of free alcohols with intermediate ozonides, see: Jung, M. E.; Davidov, P. Org. Lett. 2001, 3, 627.
- (2001) Org. Lett. , vol.3 , pp. 627
- Jung, M.E.¹ Davidov, P.²

43
- 9644292316
- Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 7538
- Gao, Y.¹ Sharpless, K.B.²

44
- 0030069953
- Derwing, C.; Hoppe, D. Synthesis 1996, 149.
- (1996) Synthesis , pp. 149
- Derwing, C.¹ Hoppe, D.²

45
- 0000920450
- Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3231
- Beak, P.¹ Kerrick, S.T.² Wu, S.³ Chu, J.⁴

46
- 33845278140
- Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 3560
- Evans, D.A.¹ Chapman, K.T.² Carreira, E.M.³

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