Facile Synthesis of Functionalised β-Lactones; Novel Cyclisations of Chromium Carbene Complexes with Propargylic Alcohols

Synlett

Volumn 1996, Issue 12, 1996, Pages 1184-1186

  Harrity, Joseph P A ^a   Heron, Nicola M ^a   Kerr, William J ^a   McKendry, Sharon ^a   Middlemiss, David ^b   Scott, James S ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002240611     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5711     Document Type: Article

References (54)

1. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
2. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
3. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
4. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
5. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
6. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
7. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
8. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
9. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
10. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
11. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
12. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
13. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
14. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
15. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
16. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
17. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
18. For review on the Dötz annulation reaction: a) Wulff, W. D. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: New York, 1991; p 1065. b) Harrington, P. J. Transition Metals in Total Synthesis; Wiley: New York. 1990; p 346. c) Dötz, K. H. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer: Berlin, 1988; p. 85. d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. e) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689. f) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. For further synthetic applications see: g) Ref. 4 and 5 in Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P. Mitchell, J.; Clardy, J. Organometallics, 1994, 13, 102. h) Ref. 6 in Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. i) Beddoes, R. L.; King, J. D.; Quayle, P. Tetrahedron Lett. 1995, 36, 3027. j) Mori, M.; Kuriyama, K.; Ochifuji, N.; Watanuki, S. Chem. Lett. 1995, 615. k) Gross, M. F.; Finn, M. G. J. Am. Chem. Soc. 1994, 116, 10921. l) Bao, J.; Wulff, W. D.; Dragisich, V.; Wenglowsky, S.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7616. m) Chamberlin, S.; Wulff, W. D.; Bax, B. Tetrahedron 1993, 49, 5531. n) Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125. o) Chamberlin, S.; Wulff, W. D. J. Am. Chem. Soc. 1992, 114, 10667. p) Bao, J.; Dragisich, V.; Wenglowsky, S.; Wulff, W. D. J. Am. Chem. Soc. 1991, 113, 9873. q) King, J. D.; Quayle, P. Tetrahedron Lett. 1991, 32, 7759. r) Gilbertson, S. R.; Wulff, W. D. Synlett 1989, 47.
19. a) Harrity, J. P. A.; Kerr, W. J.; Middlemiss, D. Tetrahedron 1993, 49, 5565.
20. b) Harrity, J. P. A.; Kerr, W. J.; Middlemiss, D. Tetrahedron Lett. 1993, 34, 2995.
21. Other workers have also now applied our modified Dötz techniques with some success: a) Painter, J. E.; Quayle, P.; Patel, P. Tetrahedron Lett. 1995, 36, 8089. b) Neidlein, R.; Gürtler, S.; Krieger, C. Helv. Chim. Acta 1994, 77, 2303.
22. Other workers have also now applied our modified Dötz techniques with some success: a) Painter, J. E.; Quayle, P.; Patel, P. Tetrahedron Lett. 1995, 36, 8089. b) Neidlein, R.; Gürtler, S.; Krieger, C. Helv. Chim. Acta 1994, 77, 2303.
23. Harrity, J. P. A.; Kerr, W. J.; Middlemiss, D.; Scott, J. S. J. Organomet. Chem. In press.
24. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
25. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
26. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
27. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
28. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
29. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
30. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
31. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
32. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
33. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
34. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
35. Knowing that alkoxyalkynes had previously been shown to be poor substrates in the Dötz cyclisation the more favourable conditions for such alkynes, developed by Yamashita, were employed for our initial annulation attempts in this programme: a) Yamashita, A.; Toy, A.; Tetrahedron Lett. 1986, 27, 3471. b) Yamashita, A. J. Am. Chem. Soc. 1985, 107, 5823. c) Yamashita, A.; Scahill, T. A.; Toy, A. Tetrahedron Lett. 1985, 26, 2969. d) Flitsch, W.; Lauterwein, J.; Micke, W. Tetrahedron Lett. 1989, 30, 1633. e) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1991, 56, 2115. f) Boger, D. L.; Jacobson, I. C. J. Org. Chem. 1990, 55, 1919. g) Boger, D. L.; Jacobson, I. C. Tetrahedron Lett. 1989, 30, 2037. See also: h) King, J.; Quayle, P.; Malone, J. F. Tetrahedron Lett. 1990, 31, 5221. i) Bauta, W. E.; Wulff, W. D.; Pavkovic, S. F.; Zaluzec, E. J. J. Org. Chem. 1989, 54, 3249. j) Chan, K. S.; Wulff, W. D. J. Am. Chem. Soc. 1986, 108, 5229. k) Yamashita, A.; Scahill, T. A.; Chidester, C. G. Tetrahedron Lett. 1985, 26, 1159. l) Wulff, W. D.; Chan, K.-S.; Tang, P.-C. J. Org. Chem. 1984, 49, 2293.
36. 1H NMR spectral studies.
37. Product 8 was isolated as a 2:1 mixture of isomers around the enol ether double bond.
38. Following the submission of this paper, in an isolated example a single β-lactone has been reported as being formed in low yield, by an analogous process: Ishibashi, T.; Ochifuji, N; Mori, M. Tetrahedron Lett. 1996, 37, 6165.
39. a) McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346.
40. b) Wulff, W. D.; Bax, B. M.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P.; Mitchell, J.; Clardy, J. Organometallics 1994, 13, 102.
41. c) Anderson, B. A.; Bao, J.; Brandvold, T. A.; Challener, C. A.; Wulff, W. D.; Xu, Y.-C.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10671.
42. 3N in THF) the acylated phenol is usually formed (e.g. Scheme 1).
43. Dötz, K. H.; Sturm, W. J. Organomet. Chem. 1985, 285, 205.
44. During the completion of our experimental studies a single example of a β-lactam forming reaction, by an analogous process, was reported: Ochifuji, N.; Mori, M. Tetrahedron Lett. 1995, 36, 9501.
45. Fischer, E. O.; Kreiter, C. G.; Kollmeier, H. J.; Müller, J.; Fischer, R. D. J. Organomet. Chem. 1971, 28, 237.
46. 2O gave the optimum yield in the majority of cases tried.
47. All compounds exhibited satisfactory analytical and spectral data.
48. a) Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080.
49. b) Ingold, C. K. J. Chem. Soc. 1921, 119, 305.
50. c) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
51. Milstien, S.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 9158.
52. 5: C, 68.66; H, 7.28. Found C, 68.67; H, 7.28%.
53. Complex 18 is readily prepared from 1,3-dimethoxybenzene and n-butyllithium in ether, followed by reaction with hexacarbonyl-chromium in THF, and subsequent treatment with triethyloxonium tetrafluoroborate in degassed water; 15.86mmol scale, 80% yield.
54. Kennedy, A. R.; Kerr, W. J.; McKendry, S. Manuscript submitted.