Substituent-control of stereoselectivity in the reaction of allylic tins. Anti-selective Lewis acid-promoted reaction toward aldehydes

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3701-3704

  Nishigaichi, Yutaka ^a   Ishida, Noriyuki ^a   Nishida, Masahiro ^a   Takuwa, Akio ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; BENZALDEHYDE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029920186     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00645-4     Document Type: Article

References (18)

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2. For reviews, see; Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron, 1993, 49, 7395-7426. Yamamoto, Y.; Shida, N. Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M. Ed.; JAI Press: London, 1994; p. 1-44. Yamamoto, Y.; Asao, N. Chem. Rev., 1993, 93, 2257-2278.
3. For reviews, see; Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron, 1993, 49, 7395-7426. Yamamoto, Y.; Shida, N. Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M. Ed.; JAI Press: London, 1994; p. 1-44. Yamamoto, Y.; Asao, N. Chem. Rev., 1993, 93, 2257-2278.
4. For reviews, see; Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron, 1993, 49, 7395-7426. Yamamoto, Y.; Shida, N. Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M. Ed.; JAI Press: London, 1994; p. 1-44. Yamamoto, Y.; Asao, N. Chem. Rev., 1993, 93, 2257-2278.
5. Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc., 1980, 102, 7107-7109. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron, 1984, 40, 2239-2246.
6. Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc., 1980, 102, 7107-7109. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron, 1984, 40, 2239-2246.
7. Keck, G. E.; Savin, K. A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem., 1994, 59, 7889-7896.
8. Mikami, K.; Kawamoto, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun., 1990, 1161-1163.
9. Marshall, J. A.; Jablonowski, J. A.; Luke, G. P. J. Org. Chem., 1994, 59, 7825-7832. Marshall J. A.; Wang, X. J. Org. Chem., 1992, 57, 1242-1252. Gung, B. W.; Smith, D. T.; Wolf, M. A. Tetrahedron Lett., 1991, 32, 13-16.
10. Marshall, J. A.; Jablonowski, J. A.; Luke, G. P. J. Org. Chem., 1994, 59, 7825-7832. Marshall J. A.; Wang, X. J. Org. Chem., 1992, 57, 1242-1252. Gung, B. W.; Smith, D. T.; Wolf, M. A. Tetrahedron Lett., 1991, 32, 13-16.
11. Marshall, J. A.; Jablonowski, J. A.; Luke, G. P. J. Org. Chem., 1994, 59, 7825-7832. Marshall J. A.; Wang, X. J. Org. Chem., 1992, 57, 1242-1252. Gung, B. W.; Smith, D. T.; Wolf, M. A. Tetrahedron Lett., 1991, 32, 13-16.
12. Nishigaichi, Y.; Takuwa, A. Chem. Lett., 1994, 1429-1432.
13. In this report, the prefix cis refers to the geometry between the stannylmethyl group and the substituent X at the 3-position of allylic tins.
14. Nishigaichi, Y.; Ishida, N.; Takuwa, A. Bull. Chem. Soc. Jpn., 1994, 67, 274-276.
15. 4 oxidation, methylation and deprotection) and the one derived from the product of entry 9 in Table 1 (methylation and ozonolysis) showed that they had different stereochemistry. (formula presented) (c) From refs. 9 (a) and (b), the following reaction was confirmed to give the anti-isomers, which were spectroscopically compared to the products in Tables 1 and 2 and Scheme 2. (formula presented)
16. Koreeda, M.; Tanaka, Y. Tetrahedron Lett., 1987, 28, 143-146.
17. Heathcock, C. H.; Hug, K. T.; Flippin, L. A. Tetrahedron Lett., 1984, 25, 5973-5976.
18. 3 because the preference may be determined by the combination of steric and electronic factors of X, Y and R. Therefore, the reason for the present marked change in the stereoselectivity is not wholly clear yet.