Carbonyl allenylations and propargylations by 3-chloro-1-propyne or 2-propynyl mesylates with tin(IV) chloride and tetrabutylammonium iodide

Synlett

Volumn , Issue 11, 2003, Pages 1713-1715

  Masuyama, Yoshiro ^a   Watabe, Akiko ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

Allenylations; Nucleophilic additions; Organometallic reagents; Propargylations; Tin(IV) chloride

Indexed keywords

3 CHLORO 1 PROPYNE; ALDEHYDE; ALKADIENE; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; CARBONYL DERIVATIVE; DICHLOROMETHANE; MESYLIC ACID DERIVATIVE; TETRABUTYLAMMONIUM; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0042912899     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41012     Document Type: Article

References (24)

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18. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
19. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
20. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
21. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
22. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
23. For representative selective carbonyl allenylations and propargylations, see: (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939. (b) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. (d) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392. (e) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (f) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449; and references cited therein.
24. 3): δ = 2.08 (t, J = 2.5 Hz, 1 H), 2.35 (d, J = 3.0 Hz, 1 H), 2.63 (ddd, J = 11, 2.5, 1.0 Hz, 1 H), 2.67 (dd, J = 11, 2.5 Hz, 1 H), 4.86-4.91 (m, 1 H), 7.27-7.45 (m, 5 H).