메뉴 건너뛰기




Volumn 120, Issue 34, 1998, Pages 8647-8655

Iridium complex-catalyzed allylic alkylation of allylic esters and allylic alcohols: Unique regio- and stereoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; ESTER DERIVATIVE; IRIDIUM COMPLEX;

EID: 0032475412     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981560p     Document Type: Article
Times cited : (224)

References (123)
  • 2
    • 0003625966 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (b) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Hegedus, L.S.1
  • 30
    • 0000222280 scopus 로고    scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4244
    • Takaya, H.1    Naota, T.2    Murahashi, S.-I.3
  • 31
    • 0002596809 scopus 로고    scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1998) J. Org. Chem. , vol.63 , pp. 4
    • Murakami, M.1    Itami, K.2    Ubukata, M.3    Tsuji, L.4    Ito, Y.5
  • 32
    • 0001390574 scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1995) Organometallics , vol.14 , pp. 4418
    • Chatani, N.1    Yamaguchi, S.2    Fukumoto, Y.3    Murai, S.4
  • 33
    • 0000517520 scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9710
    • Chatani, N.1    Ikeda, S.2    Ohe, K.3    Murai, S.4
  • 34
    • 0026493891 scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7119
    • Jun, C.-H.1    Crabtree, R.H.2
  • 35
    • 0000619969 scopus 로고
    • For a stoichiometric reaction see
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5145
    • Rappoli, B.J.1    Churchill, M.R.2    Janik, T.S.3    Rees, W.M.4    Atwood, J.D.5
  • 36
    • 0001061025 scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8275
    • Schwiebert, K.E.1    Stryker, J.M.2
  • 37
    • 0001041890 scopus 로고
    • For a catalytic reaction see: (a) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244. (b) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, L; Ito, Y. J. Org. Chem. 1998, 63, 4. (c) Chatani, N.; Yamaguchi, S.; Fukumoto, Y.; Murai, S. Organometallics 1995, 14, 4418. (d) Chatani, N.; Ikeda, S.; Ohe, K.; Murai, S. J. Am. Chem. Soc. 1992, 114, 9710. (e) Jun, C.-H.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119. (f) Rappoli, B. J.; Churchill, M. R.; Janik, T. S.; Rees, W. M.; Atwood, J. D. J. Am. Chem. Soc. 1987, 109, 5145. For a stoichiometric reaction see: (g) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275. (h) Wakefield, J. B.; Stryker, J. M. J. Am. Chem. Soc. 1991, 113, 7057.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7057
    • Wakefield, J.B.1    Stryker, J.M.2
  • 38
    • 3543103449 scopus 로고    scopus 로고
    • See ref 1e, p 25
    • See ref 1e, p 25.
  • 39
    • 6844254916 scopus 로고    scopus 로고
    • For review see: (a) Trost, B. M.; Varanken, D. L. V. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 797. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 585.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, B.M.1    Varanken, D.L.V.2
  • 40
    • 0003441482 scopus 로고
    • John Wiley & Sons: New York
    • For review see: (a) Trost, B. M.; Varanken, D. L. V. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 797. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 585.
    • (1995) Palladium Reagents and Catalysts , pp. 290
    • Tsuji, J.1
  • 41
    • 0003321649 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • For review see: (a) Trost, B. M.; Varanken, D. L. V. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 797. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 585.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 797
    • Harrington, P.J.1
  • 42
    • 0000276556 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For review see: (a) Trost, B. M.; Varanken, D. L. V. Chem. Rev. 1996, 96, 395. (b) Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995; p 290. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 797. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 585.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 585
    • Godleski, S.A.1
  • 82
    • 33751158980 scopus 로고
    • For examples of allylic alkylation of a terminaly substituted π-allyl palladium intermediate, see: (a) Sjogren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730. (c) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1980, 21, 4437. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416. (e) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
    • (1994) Organometallics , vol.13 , pp. 1963
    • Sjogren, M.P.T.1    Hansson, S.2    Akermark, B.3    Vitagliano, A.4
  • 83
    • 33847086796 scopus 로고
    • For examples of allylic alkylation of a terminaly substituted π-allyl palladium intermediate, see: (a) Sjogren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730. (c) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1980, 21, 4437. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416. (e) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4730
    • Trost, B.M.1    Verhoeven, T.R.2
  • 84
    • 0000562690 scopus 로고
    • For examples of allylic alkylation of a terminaly substituted π-allyl palladium intermediate, see: (a) Sjogren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730. (c) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1980, 21, 4437. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416. (e) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 4437
    • Fiaud, J.C.1    Malleron, J.L.2
  • 85
    • 0000575896 scopus 로고
    • For examples of allylic alkylation of a terminaly substituted π-allyl palladium intermediate, see: (a) Sjogren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730. (c) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1980, 21, 4437. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416. (e) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3416
    • Trost, B.M.1    Weber, L.2    Strege, P.E.3    Fullerton, T.J.4    Dietsche, T.J.5
  • 86
    • 33947094963 scopus 로고
    • For examples of allylic alkylation of a terminaly substituted π-allyl palladium intermediate, see: (a) Sjogren, M. P. T.; Hansson, S.; Akermark, B.; Vitagliano, A. Organometallics 1994, 13, 1963. (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730. (c) Fiaud, J. C.; Malleron, J. L. Tetrahedron Lett. 1980, 21, 4437. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416. (e) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3426.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3426
    • Trost, B.M.1    Weber, L.2    Strege, P.E.3    Fullerton, T.J.4    Dietsche, T.J.5
  • 92
    • 3543063763 scopus 로고    scopus 로고
    • note
    • Use of a steric demanding nucleophile increased the selectivity of alkylation at the unsubstituted allylic terminus; see ref 14e.
  • 102
    • 3543069631 scopus 로고    scopus 로고
    • note
    • Akermark reported that 2,9-disubstituted-1,10-phenanthroline could stabilize anti π-allyl palladium complex and its use for Pd-catalyzed allylic alkylation. The reaction of (Z)-2-hexenyl acetate with diethyl sodiomethylmalonate gave (Z)-product in 72% selectivity; see ref 14a.
  • 103
    • 0001124147 scopus 로고
    • For a mechanism with double inversion of configuration, see: (a) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (b) Fiaud, J. C.; Legros, J. Y. J. Org. Chem. 1987, 52, 1907. A mechanism with double retention of configuration cannot be ruled out; see ref 10h.
    • (1986) J. Org. Chem. , vol.51 , pp. 723
    • Hayashi, T.1    Yamamoto, A.2    Hagihara, T.3
  • 104
    • 0000565225 scopus 로고
    • A mechanism with double retention of configuration cannot be ruled out; see ref 10h
    • For a mechanism with double inversion of configuration, see: (a) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (b) Fiaud, J. C.; Legros, J. Y. J. Org. Chem. 1987, 52, 1907. A mechanism with double retention of configuration cannot be ruled out; see ref 10h.
    • (1987) J. Org. Chem. , vol.52 , pp. 1907
    • Fiaud, J.C.1    Legros, J.Y.2
  • 105
    • 3543096549 scopus 로고    scopus 로고
    • A complex of terminal alkenes is more stable than that of internal alkenes: see ref 20b
    • A complex of terminal alkenes is more stable than that of internal alkenes: see ref 20b.
  • 110
    • 3543085923 scopus 로고    scopus 로고
    • note
    • 3)], To avoid a steric repulsion of the substituted allylic terminus, triphenyl phosphite coordinates trans to the substituted allylic terminus.
  • 112
    • 3543081256 scopus 로고    scopus 로고
    • note
    • 9-catalyzed reaction of (E)-crotyl acetate with dimethyl sodiomalonate gave the product from the alkylation at the substituted allylic terminus as a major product, whereas the same reaction of (Z)-crotyl acetate gave the product from the alkylation at the unsubstituted allylic terminus as a major product; see ref 11 d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.