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Journal of the American Chemical Society

Volumn 118, Issue 50, 1996, Pages 12528-12535

Stereoselective radical carbon-carbon bond forming reactions of β-alkoxy esters: Atom and group transfer allylations under bidentate chelation controlled conditions

(4) Guindon, Y a,b Guerin B a,b Chabot, C c Ogilvie, W c

a CLIN RESEARCH INSTITUTE OF MONTREAL (Canada)

b UNIVERSITÉ DE MONTRÉAL (Canada)

c BOEHRINGER INGELHEIM CANADA LTD (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030479215 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja9541241 Document Type: Article

Times cited : (66)

References (76)

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29
- 0041664450
- Bidendate: (a) Guindon, Y.; Lavallée, J. -F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. (b) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett. 1995, 449-451. (c) Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89-96. (d) Toni, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. (e) Rück, K.; Kunz, H. Synthesis, 1993, 1018. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988. (g) Yamamoto, Y.; Onuki, S; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (h) Wu, J. H.; Radinov, R.; Porter, N. A.; J. Am. Chem. Soc. 1995, 117, 11029-11030. (i) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779-10780. (j) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190-192. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064.
- (1995) Synlett , pp. 449-451
- Guindon, Y.¹ Guérin, B.² Chabot, C.³ Mackintosh, N.⁴ Ogilvie, W.W.⁵

30
- 0002535530
- Bidendate: (a) Guindon, Y.; Lavallée, J. -F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. (b) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett. 1995, 449-451. (c) Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89-96. (d) Toni, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. (e) Rück, K.; Kunz, H. Synthesis, 1993, 1018. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988. (g) Yamamoto, Y.; Onuki, S; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (h) Wu, J. H.; Radinov, R.; Porter, N. A.; J. Am. Chem. Soc. 1995, 117, 11029-11030. (i) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779-10780. (j) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190-192. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064.
- (1996) Pure Appl. Chem. , vol.68 , pp. 89-96
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31
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- Bidendate: (a) Guindon, Y.; Lavallée, J. -F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. (b) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett. 1995, 449-451. (c) Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89-96. (d) Toni, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. (e) Rück, K.; Kunz, H. Synthesis, 1993, 1018. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988. (g) Yamamoto, Y.; Onuki, S; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (h) Wu, J. H.; Radinov, R.; Porter, N. A.; J. Am. Chem. Soc. 1995, 117, 11029-11030. (i) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779-10780. (j) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190-192. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064.
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- Toni, T.¹ Watanabe, Y.² Tsusaka, M.³ Ueno, Y.⁴

32
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- Bidendate: (a) Guindon, Y.; Lavallée, J. -F.; Llinas-Brunet, M.; Horner, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. (b) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett. 1995, 449-451. (c) Guindon, Y.; Guérin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89-96. (d) Toni, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465. (e) Rück, K.; Kunz, H. Synthesis, 1993, 1018. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987-988. (g) Yamamoto, Y.; Onuki, S; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422. (h) Wu, J. H.; Radinov, R.; Porter, N. A.; J. Am. Chem. Soc. 1995, 117, 11029-11030. (i) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779-10780. (j) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190-192. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064.
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33
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- (1994) J. Chem. Soc., Chem. Commun. , pp. 987-988
- Nagano, H.¹ Kuno, Y.²

34
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- Yamamoto, Y.¹ Onuki, S.² Yumoto, M.³ Asao, N.⁴

35
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- Wu, J.H.¹ Radinov, R.² Porter, N.A.³

36
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- Sibi, M.P.¹ Jasperse, C.P.² Ji, J.³

37
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38
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- Tables of the chemical shift data used to make these correlations can be found in the supplementary material.

59
- 0000099179
- A similar trend has been observed in the case of reduction. See ref 4 and: Gouzoules, F. H.; Whitney, R. A. J. Org. Chem. 1986, 51, 2024-2030.
- (1986) J. Org. Chem. , vol.51 , pp. 2024-2030
- Gouzoules, F.H.¹ Whitney, R.A.²

60
- 0024835729
- This reagent is reported to give allyl adducts through an atom transfer/elimination sequence, (a) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (b) Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856-862. (c) Hirao, T.; Fujii, T.; Ohshiro, Y. Tetrahedron Lett. 1994, 35, 8005-8008 and refs cited therein.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8872-8878
- Curran, D.P.¹ Chen, M.-H.² Spletzer, E.³ Seong, C.M.⁴ Chang, C.-T.⁵

61
- 0000836057
- This reagent is reported to give allyl adducts through an atom transfer/elimination sequence, (a) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (b) Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856-862. (c) Hirao, T.; Fujii, T.; Ohshiro, Y. Tetrahedron Lett. 1994, 35, 8005-8008 and refs cited therein.
- (1995) J. Org. Chem. , vol.60 , pp. 856-862
- Hwu, J.R.¹ Chen, C.N.² Shiao, S.-S.³

62
- 0027988787
- and refs cited therein
- This reagent is reported to give allyl adducts through an atom transfer/elimination sequence, (a) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (b) Hwu, J. R.; Chen, C. N.; Shiao, S.-S. J. Org. Chem. 1995, 60, 856-862. (c) Hirao, T.; Fujii, T.; Ohshiro, Y. Tetrahedron Lett. 1994, 35, 8005-8008 and refs cited therein.
- (1994) Tetrahedron Lett. , vol.35 , pp. 8005-8008
- Hirao, T.¹ Fujii, T.² Ohshiro, Y.³

63
- 12644315844
- note
- Ratios were determined by GC using crude reaction mixtures. These ratios were comparable to those obtained by NMR spectroscopy. In the case of the phenyl and cyclohexyl substituted secondary substrates (9 and 15, Table 2, entries 1 and 3), the GC and NMR results were calibrated using product mixtures of varying composition.

64
- 0025784933
- A similar drop in reactivity has been previously observed for other tertiary iodides. Curran, D. P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189-6196.
- (1991) Tetrahedron , vol.47 , pp. 6189-6196
- Curran, D.P.¹ Kim, D.² Ziegler, C.³

65
- 0001403744
- Brown, H. C.; Midland, M. M.; Kabalka, G. W. J. Am. Chem. Soc. 1971, 93, 1024-1025.
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 1024-1025
- Brown, H.C.¹ Midland, M.M.² Kabalka, G.W.³

66
- 12644303057
- unpublished results
- We are on one hand trying to avoid this reaction pathway and on the other hand trying to optimize it for a different application. Guindon, Y.; Yoakim, C.; Soucy, F. unpublished results.
- Guindon, Y.¹ Yoakim, C.² Soucy, F.³

67
- 12644275255
- Details of this reaction including proof of configuration will be published elsewhere
- Details of this reaction including proof of configuration will be published elsewhere.

68
- 0026462897
- For examples of group transfer reactions involving selenium see: (a) Beyers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 23, 6953-6954. (b) Curran, D. P.; Martin-Esker, A. A.; Ko, S.-B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691-4695 and refs cited therein. See also ref 10a.
- (1992) Tetrahedron Lett. , vol.23 , pp. 6953-6954
- Beyers, J.H.¹ Harper, B.C.²

69
- 0001098565
- and refs cited therein. See also ref 10a
- For examples of group transfer reactions involving selenium see: (a) Beyers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 23, 6953-6954. (b) Curran, D. P.; Martin-Esker, A. A.; Ko, S.-B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691-4695 and refs cited therein. See also ref 10a.
- (1993) J. Org. Chem. , vol.58 , pp. 4691-4695
- Curran, D.P.¹ Martin-Esker, A.A.² Ko, S.-B.³ Newcomb, M.⁴

70
- 12644300487
- The reaction mixture contained ca. 40% of the α-hydroxy-β-alkoxy ester
- The reaction mixture contained ca. 40% of the α-hydroxy-β-alkoxy ester.

71
- 12644305729
- note
- We have found in several radical processes that there is often a large difference in reactivity between syn and anti iodide diastereomers. The fact that two such diastereomers can have such dissimilar behaviors is very intriguing, and we are currently investigating this phenomenon.

72
- 12644296830
- note
- The same intermediate was observed when syn phenylselenide 40 was used.

73
- 0000004695
- Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403-409.
- (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 403-409
- Nozaki, K.¹ Oshima, K.² Utimoto, K.³

74
- 12644271040
- note
- This hydroxylation pathway was not observed in the analogous reaction performed using allyltributyltin. See ref 7b.

75
- 12644291787
- note
- For a recent example of the effect of the nature of Lewis acid on reaction pathways see ref 7k.

76
- 12644306723
- note
- 2EtN and diisopropylatnine were distilled from calcium hydride. Methanol was distilled from magnesium.

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