Stereoselective synthesis of α-disubstituted cyclopentanones by palladium-catalyzed rearrangement of allenylcyclobutanols with aryl halides

Tetrahedron

Volumn 58, Issue 39, 2002, Pages 7839-7846

  Yoshida, Masahiro ^a   Sugimoto, Kenji ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Cyclopentanones; Palladium and compounds; Rearrangements; Ring transformations

Indexed keywords

2 (4 ACETYLPHENYLVINYL) 2 METHYL 3 PHENYLCYCLOPENTANONE; 2 [1 (4 METHOXYPHENYL)VINYL] 2 PHENYL 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 (1 METHYLENE 2 PHENYL 2 PROPENYL) 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 (1 PHENYLVINYL) 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 (4 METHOXYPHENYLVINYL) 3 (3 HYDROXYPROPYL) 3 METHYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [1 (1 NAPHTHYL)VINYL] 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [1 (4 METHOXYPHENYL)VINYL] 3 (3 TERT BUTYLDIPHENYLSILOXYPROPYL) 3 METHYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [1 (4 METHOXYPHENYL)VINYL] 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [1 (4 METHYLPHENYL)VINYL] 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [1 (4 NITROPHENYL)VINYL] 3 PHENYLCYCLOPENTAN 1 ONE; 2 METHYL 2 [3,4 (METHYLENEDIOXY)PHENYL]VINYL 3 PHENYLCYCLOPENTAN 1 ONE; BUTANOL; CYCLOPENTANONE DERIVATIVE; HALIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; SILYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037163335     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00910-9     Document Type: Article

References (32)

1. For reviews, see: (a) Corey E.J., Guzman-Perez A. Angew. Chem. Int. Ed. 37:1998;388 (b) Fuji K. Chem. Rev. 93:1993;2037 (c) Martin S.F. Tetrahedron. 36:1980;419. and references cited therein.
2. For reviews, see: (a) Corey E.J., Guzman-Perez A. Angew. Chem. Int. Ed. 37:1998;388 (b) Fuji K. Chem. Rev. 93:1993;2037 (c) Martin S.F. Tetrahedron. 36:1980;419. and references cited therein.
3. For reviews, see: (a) Corey E.J., Guzman-Perez A. Angew. Chem. Int. Ed. 37:1998;388 (b) Fuji K. Chem. Rev. 93:1993;2037 (c) Martin S.F. Tetrahedron. 36:1980;419. and references cited therein.
4. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
5. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
6. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
7. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
8. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
9. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
10. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
11. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
12. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
13. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
14. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
15. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
16. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
17. For the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Boontanonda P., Grigg R. J. Chem. Soc., Chem. Commun. 1977;583 (b) Clark G.R., Thiensathit S. Tetrahedron Lett. 26:1985;2503 (c) Liebeskind L.S., Mitchell D., Foster S.B. J. Am. Chem. Soc. 109:1987;7908 (d) Demuth M., Pandey B., Wietfeld B., Said H., Viader J. Helv. Chim. Acta. 71:1988;1392 (e) de Almeida Barbosa L.-C., Mann J. J. Chem. Soc., Perkin Trans. 1. 1990;177 (f) Mitchell D., Liebeskind L.S. J. Am. Chem. Soc. 112:1990;291 (g) Kim S., Uh K.H., Lee S., Park J.H. Tetrahedron Lett. 32:1990;3395 (h) Nemoto H., Shiraki M., Fukumoto K. Synlett. 1994;599 (i) Nemoto H., Nagamochi M., Fukumoto K. J. Org. Chem. 59:1994;74-79 (j) Nemoto H., Miyata J., Fukumoto K. Tetrahedron. 52:1996;10363 (k) Nemoto H., Miyata J., Yoshida M., Raku N., Fukumoto K. J. Org. Chem. 62:1997;7850 (l) Yoshida M., Nemoto H., Ihara M. Tetrahedron Lett. 40:1999;8583 (m) Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645 (n) Larock R.C., Reddy C.K. Org. Lett. 2:2000;3325.
18. For the palladium-catalyzed hetero- and carbocyclic ring expansion reactions, see: (a) Jeong I.-Y., Nagao Y. Tetrahedron Lett. 39:1998;8677 (b) Jeong I.-Y., Nagao Y. Synlett. 1999;576.
19. For the palladium-catalyzed hetero- and carbocyclic ring expansion reactions, see: (a) Jeong I.-Y., Nagao Y. Tetrahedron Lett. 39:1998;8677 (b) Jeong I.-Y., Nagao Y. Synlett. 1999;576.
20. For the ruthenium-catalyzed ring expansion reaction of allenylcyclobutanols, see: Yoshida M., Sugimoto K., Ihara M. Tetrahedron Lett. 42:2001;3877.
21. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
22. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
23. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
24. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
25. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
26. Applications of the palladium-catalyzed ring expansion reactions to natural products syntheses, see: (a) Nemoto H., Nagamochi M., Fukumoto K. J. Chem. Soc., Perkin Trans. 1. 1993;2329 (b) Nemoto H., Nagamochi M., Ishibashi H., Fukumoto K. J. Org. Chem. 59:1994;74 (c) Nemoto H., Miyata J., Ihara M. Tetrahedron Lett. 40:1999;1933 (d) Nemoto H., Takahashi E., Ihara M. Org. Lett. 1:1999;517 (e) Nemoto H., Yoshida M., Fukumoto K., Ihara M. Tetrahedron Lett. 40:1999;907 (f) Yoshida M., Ismail A.-H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1:2000;2629.
27. Nemoto H., Yoshida M., Fukumoto K. J. Org. Chem. 62:1997;6450.
28. . A part of this work has been published as a preliminary communication: Yoshida M., Sugimoto K., Ihara M. Tetrahedron Lett. 41:2000;5089.
29. Nemoto H., Shiraki M., Fukumoto K. J. Org. Chem. 61:1996;1347.
30. Owada Y., Matsuo T., Iwasawa N. Tetrahedron. 53:1997;11069.
31. In the ring expansion step, the palladium would be placed rear side to undergo anti attack of the migrating group.
32. 3 mechanism.