Erythro-Selective Addition of Crotyltrialkyltins to Aldehydes Regardless of the Geometry of the Crotyl Unit. Stereoselection Independent of the Stereochemistry of Precursors

Journal of the American Chemical Society

Volumn 102, Issue 23, 1980, Pages 7107-7109

  Yamamoto, Yoshinori ^a   Yatagai, Hidetaka ^a   Naruta, Yoshinori ^a   Maruyama, Kazuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847085986     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00543a040     Document Type: Article

References (37)

1. For review articles, see: (a) Bartlett, P.A. Tetrahedron, 1980, 36, 3.
2. Masamune, S. Atdrichimica Acta 1978, 11, 23.
3. Li: (a) Kleschick, W.A.; Buse, C.T.; Heathcock, C.H. J. Am. Chem. Soc. 1977, 99, 247.
4. Buse, C.T.; Heathcock, C.H. J. Am. Chem. Soc. 1977, 99, 8109.
5. Meyers, A.L.; Reider, P.J. J. Am. Chem. Soc. 1979, 101, 2501.
6. Dubois, J.E.; Fellmann, P. Tetrahedron Lett. 1975, 1225.
7. Mulzer, J.; Segner, J.; Bruntrup, G. Tetrahedron Lett. 1977, 4651.
8. Heathcock, C.H.; Buse, C.T.; Kleschick, W.A.; Pirrung, M.C.; Sohn, J.E.; Lampe, J.J. Org. Chem. 1980, 45, 1066. Li, Mg, and Zn:
9. House, H.O.; Crumrine, D.S.; Teranishi, A.Y.; Olmstead, H.D. J. Am. Chem. Soc. 1973, 95, 3310. B.;
10. Fenzl, W.; Kster, R.; Zimmermann, H.J. Justus Liebigs Ann. Chem. 1975, 2201.
11. Masamune, S.; Mori, D.; Horn, D.V.; BroolK, D.W. Tetrahedron Lett. 1979, 1665.
12. Hirama, M.; Masamune, S. Tetrahedron Lett. 1979, 2225.
13. Horn, D.V.; Masamune, S. Tetrahedron Lett. 1979, 2229.
14. Hirama, M.; Garvey, D.S.; Lu, L.D.; Masamune, S. Tetrahedron Lett. 1979, 3937.
15. Evans, D.A.; Vogel, E.; Nelson, J.V. J. Am. Chem. Soc. 1979, 101, 6120. Al;
16. Jeffrey, E.A.; Meisters, A.; Mole, T.J. J. Organomet. Chem, 1974, 74, 313. Aluminum (Z)-enolates give threo derivatives in contrast with other enolates.
17. Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H.J. Am. Chem. Soc. 1977, 99, 7705. Si and Ti:
18. Mukaiyama, T.; Banno, K.; Narasaka, K.J. Am. Chem. Soc. 1974, 96. 7505.
19. Chan, T.H.; Aida, T.; Lau, P.W.K.; Gorys, V.; Harpp, D.N. Tetrahedron Lett. 1979, 4029.
20. Li: (a) Hayashi, T.; Fujitaka, N.; Oishi, T.; Takeshima, T. Tetrahedron Utt. 1980, 303. B:
21. Hoffmann, R.W.; Ladner, W. Tetrahedron Utt. 1979, 4653.
22. Hoffmann, R.W.; Zeiss, H.J. Angew. Chem., Int. Ed. Engl. 1979, IS, 306. Al:
23. Collum, D.B.; McDonald, J.H., III; Still, W.C. J. Am. Chem. Soc. 1980,102, 2118. Sn:
24. Servens, C.; Pereyre, M.J. Organomet. Chem. 1972, 35, c20.
25. Yatagai, H.; Yamamoto, Y.; Maruyama, K.J. Am. Chem. Soc. 1980, 102, 4548.
26. Naruta, Y.; Ushida, S.; Maruyama, K. Chem. Lett. 1979, 919.
27. Rautenstrauch, V. Helv. Chim. Acta 1974, 57, 496,
28. Abenhaim, D.; Basch, E.H.; Freon, P. Bull. Soc. Chim. Fr. 1969, 4038,4042,
29. Abenhaim, D.; Basch, E.H. C. R. Hebd. Seances Acad. Sci., Ser. C 1968, 267, 87,
30. Felkin, H.; Gault, Y.; Roussi, G. Tetrahedron 1970, 3761.
31. Kramer, G.W.; Brown, H.C. J. Org. Chem. 1977, 42, 2292.
32. On the contrary, Felkin has reported that allylic organomagnesium compounds react with carbonyl derivatives according to the mechanism of noncyclic bimolecular electrophilic substitution (Se2'). See ref 6c and Courtois, G.; Miginiac, L.J. Organomet. Chem. 1974, 69, 1, Felkin, H.; Frajerman, C. Tetrahedron Lett. 1970, 1045, Cherest, M.; Felkin, H.; Fra-jerman, C.J. Org. Chem. 1971, 379,
33. Similar consideration is made on aldol addition: Mulzer, J.; Bruntrup, G.; Finke, J.; Zippel, M.J. Am. Chem. Soc. 1979, 101, 7723,
34. In the absence of a coordinating cation, threo products are obtained from (Z)-enolates: ref 2a and Noyori, R.; Yokoyama, K.; Sakata, J.; Ku-wajima. I.; Nakamura, E.; Shimizu, M.J. Am. Chem. Soc. 1977, 99, 1265, Very low stereoselection is observed in protic media: Fellmann, P.; Dubois, J.E. Tetrahedron 1978, 34, 1349, Dubois, J.E.; Fort, J. F, J. Am. Chem. Soc. 1972, 28, 1653. See also Naruta, Y.J. Am. Chem. Soc. 1980, 102, IIH.
35. Titanium tetrachloride mediated reaction of crotyltrimethylsilane with propanal produced a mixture of erythro (60%) and threo (40%) isomers. This may be due to the fact that the affinity of Si toward oxygen atoms is higher than that of Sn, and hence that the reaction via Si involves more or less the cyclic transition state. For the affinity of Si and Sn, see: Itoh, K.; Matstjzaki, K.; Ishii, Y.J. Chem. Soc. C 1968, 2709. Itoh, K.; Fukumoto, Y.; Ishii, Y. Tetrahedron Lett. 1968, 3199. The addition of crotyl bromide to aldehydes with chromous ion provides the threo products regardless of the geometry of the starting material: Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H.J. Am. Chem. Soc. 1977,99, 3179. Buse, C.T.; Heathcock, C.H. Tetrahedron Lett. 1978, 1685.
36. Crotyltins were prepared according to M-Tchiroukhine, E.; Cadiot, P.J. Organomet. Chem. 1976, 121, 155; Tetrahedron Lett. 1976, 121, 169.
37. Note Added in Proof: In a communication that appeared subsequent to submission of this manuscript. Professor Noyori and co-workers report that an acylic transition state may be involved in the reaction of enol silyl ethers with acetals in the presence of catalytic amounts of Me3SiOTf; Murata, S.; Suzuki, M.; Noyori, R.J. Am. Chem. Soc. 1980,102, 3248. We also learned that the similar stereoselection of allylic tin derivatives was observed by Professor Koreeda, University of Michigan, private communication.