'Amphiphilic' cleavage of γ-stannyl ketones with ATPH/RLi: Application to enone fragmentation by the conjugate addition - Cleavage sequence

Angewandte Chemie - International Edition

Volumn 39, Issue 2, 2000, Pages 414-416

  Kondo, Yuichiro ^a   Kon i, Kana ^a   Iwasaki, Atsuko ^a   Ooi, Takashi ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aluminum; Cleavage reactions; Conjugate additions; Ketones; Lewis acids

Indexed keywords

KETONE DERIVATIVE; TIN DERIVATIVE;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034677047     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(20000117)39:2<414::aid-anie414>3.0.co;2-9     Document Type: Article

References (20)

1. Reviews: a) Comprehensive Organic Syntheis, Vol 6 (eds.: B. M. Trost. I. Fleming), Pergamon, Oxford. 1991, p. 1041; b) C. A. Grob, P.W. Schiess, Angew. Chem. 1967, 79, 1; Angew. Chem. Int. Ed. Engl. 1967, 6, 1.
2. Reviews: a) Comprehensive Organic Syntheis, Vol 6 (eds.: B. M. Trost. I. Fleming), Pergamon, Oxford. 1991, p. 1041; b) C. A. Grob, P.W. Schiess, Angew. Chem. 1967, 79, 1; Angew. Chem. Int. Ed. Engl. 1967, 6, 1.
3. Reviews: a) Comprehensive Organic Syntheis, Vol 6 (eds.: B. M. Trost. I. Fleming), Pergamon, Oxford. 1991, p. 1041; b) C. A. Grob, P.W. Schiess, Angew. Chem. 1967, 79, 1; Angew. Chem. Int. Ed. Engl. 1967, 6, 1.
4. For recent exemples of cleavage of C C bonds within a ring, see a) J. Grimshaw, R. J. Elaslett, J. Chem. Soc. Chem. Commun. 1974, 174; b) M. Takayanagi, N. Umamori, K. Tanino, I. Kuwajima, J. Am. Chem. Soc. 1993, 115, 12635; c) H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449: Angew. Chem. Int. Ed. Engl. 1997, 36, 2352.
5. For recent exemples of cleavage of C C bonds within a ring, see a) J. Grimshaw, R. J. Elaslett, J. Chem. Soc. Chem. Commun. 1974, 174; b) M. Takayanagi, N. Umamori, K. Tanino, I. Kuwajima, J. Am. Chem. Soc. 1993, 115, 12635; c) H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449: Angew. Chem. Int. Ed. Engl. 1997, 36, 2352.
6. For recent exemples of cleavage of C C bonds within a ring, see a) J. Grimshaw, R. J. Elaslett, J. Chem. Soc. Chem. Commun. 1974, 174; b) M. Takayanagi, N. Umamori, K. Tanino, I. Kuwajima, J. Am. Chem. Soc. 1993, 115, 12635; c) H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449: Angew. Chem. Int. Ed. Engl. 1997, 36, 2352.
7. For recent exemples of cleavage of C C bonds within a ring, see a) J. Grimshaw, R. J. Elaslett, J. Chem. Soc. Chem. Commun. 1974, 174; b) M. Takayanagi, N. Umamori, K. Tanino, I. Kuwajima, J. Am. Chem. Soc. 1993, 115, 12635; c) H. Harayama, T. Kuroki, M. Kimura, S. Tanaka, Y. Tamaru, Angew. Chem. 1997, 109, 2449: Angew. Chem. Int. Ed. Engl. 1997, 36, 2352.
8. Mass Spectrometry of Organic Ions (Ed.; F. W. McLafferty), Academic Press, New York, 1963.
9. A similar type of fragmentation was reported by Hamon et al.: D. P. G. Hamon, G. F. Taylor, R. N. Young. Synthesis 1975, 428: however, such a fragmentation has not been developed to a synthetically useful level.
10. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
11. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
12. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
13. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
14. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
15. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
16. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
17. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
18. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
19. 3AI at room temperature for 30 min. For other synthetic applications, see a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519; c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928; e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230; Angew. Chem. Int. Ed. Engl. 1997, 36, 1181; f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231; Angew. Chem. Int. Ed. Engl. 1997, 36, 1183; g) S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813; h) S. Saito, H. Yamamoto, Chem. Eur. J. 1999, 5, 1959, and references therein.
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