Preparation of tributylstannylmanganate and its addition to propargylic alcohols with high regio- and stereoselectivities

Synlett

Volumn , Issue 9, 1999, Pages 1417-1419

  Usugi, Shinichi ^a   Tang, Jun ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Conjugate addition; Propargylic alcohol; Stannylmanganate; Stannylmethylation

Indexed keywords

MANGANESE DERIVATIVE; ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL REACTION; CONJUGATION; METHYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0032866038     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2873     Document Type: Article

References (16)

1. Pereyre, M.; Quintard, J.-P.; Rahn, A. Tin in Organic Synthesis; Butterworths: London, 1987.
2. Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768-7780 and references cited therein.
3. a) Hibino, J. I.; Matsubara, S.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 2151-2154.
4. b) Nozaki, K.; Wakamatsu, K.; Nonaka, T.; Tückmantel, W.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1986, 27, 2007-2010.
5. Tang, J.; Yorimitsu, H.; Kakiya, H.; Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 9019-9022.
6. 3 with cuprate has been reported in Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617-4620. Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. Lipshutz, B. H.; Sharma, S.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 7253-7256.
7. 3 with cuprate has been reported in Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617-4620. Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. Lipshutz, B. H.; Sharma, S.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 7253-7256.
8. 3 with cuprate has been reported in Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617-4620. Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. Lipshutz, B. H.; Sharma, S.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 7253-7256.
9. That trialkylmanganate and tetraalkylmanganate may have different characters has been reported by our group and Hosomi's group. Please see: Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron, 1997, 53, 5061-5072. Hojo, M.; Harada, H.; Ito, H.; Hosomi, A. J. Chem. Soc., Chem Commun. 1997, 2077-2078.
10. That trialkylmanganate and tetraalkylmanganate may have different characters has been reported by our group and Hosomi's group. Please see: Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron, 1997, 53, 5061-5072. Hojo, M.; Harada, H.; Ito, H.; Hosomi, A. J. Chem. Soc., Chem Commun. 1997, 2077-2078.
11. 2MnLi) effectively.
12. The reaction of trimethylstannyllithium with α,β-unsaturated ketones in THF has been reported to give 1,4-adduct. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4837-4838.
13. Treatment of 8 with 2a under the identical conditions led to an allylic alcohol (E/Z = 10/1) in 50% yield without incorporation of a stannyl group.
14. 2 resulted in formation of a complex mixture.
15. Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870.
16. This work was supported by Grant-in-Aid for Scientific Research (No. 09450341) from the Ministry of Education , Science, Sports and Culture, Government of Japan.