First demonstration of helical chirality in 1,4-disubstituted (Z,Z)-1,3-dienes: R3Si-SnR'3-mediated cyclization of 1,6-diynes [11]

Journal of the American Chemical Society

Volumn 122, Issue 35, 2000, Pages 8579-8580

  Gréau, Sandra ^a   Radetich, Branko ^a   Rajanbabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; LETTER; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037652748     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0015500     Document Type: Letter

References (21)

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2. For recent reviews see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon/Elsevier: Kidlington, 1995; p 741. (d) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. For recent reviews see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon/Elsevier: Kidlington, 1995; p 741. (d) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. For recent reviews see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon/Elsevier: Kidlington, 1995; p 741. (d) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. For recent reviews see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon/Elsevier: Kidlington, 1995; p 741. (d) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
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12. (c) For a recent related reports of hydrosilylation/carbonylation, see: Chatani, N.; Fukumoto, Y.; Ida, T.; Murai, S. J. Am. Chem. Soc. 1993, 115, 11614; Ojima, I.; Lee, S.-Y. J. Am. Chem. Soc. 2000, 122, 2385 and references therein.
13. (c) For a recent related reports of hydrosilylation/carbonylation, see: Chatani, N.; Fukumoto, Y.; Ida, T.; Murai, S. J. Am. Chem. Soc. 1993, 115, 11614; Ojima, I.; Lee, S.-Y. J. Am. Chem. Soc. 2000, 122, 2385 and references therein.
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19. See Supporting Information for details, including VT NMR spectra and a discussion of criteria of purity (NMR and HPLC) of key compounds.
20. 2 carbons are also better resolved at -40°C.
21. Because of disorders in the crystal, complete solution of the structure was not possible, even though reliable data on the ammonium ion could be extracted.