Enantioselective allylation of aldehydes using tartrate ester modified allylsilanes

Chemistry Letters

Volumn , Issue 2, 1997, Pages 129-130

  Zhang, Luo Cheng ^a   Sakurai, Hideki ^a   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000758834     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.129     Document Type: Article

References (23)

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18. Preliminary results of this paper were presented at: The 68th Symposium Organic Synthesis, Japan, Tokyo, November 9-10, 1995. Very recently, a closely related work was reported: Z. Wang, D. Wang, and X. Sui, J. Chem. Soc., Chem. Commun., 1996, 2261.
19. 6Si: C, 53.14; H, 7.64%.
20. 7 have assumed the coordination of an amine to a silicon atom at the transition state, it would not be needed, since the present allylation takes place in the absence of amines.
21. The E/Z ratios of 6E and 6Z used here were 94/6 and 3/97, respectively.
22. 1H NMR to be 93/7 and 96/4, respectively. The absolute configurations of (1S, 2S)-7 and (1S, 2R)-7 were assigned by comparing the optical rotation to those in the literature: W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, and R. L. Halterman, J. Am. Chem. Soc., 112, 6339 (1990).
23. At the hexacoordinate silicon transition states, T and T' in Scheme 1, it is presumed that methyl and chlorine substituents on silicon occupy the less crowded position to avoid the steric repulsion between the substituents and the six-membered ring.