Enantioselective Synthesis of 2-Alkyl-2-methyl-3-butenenitriles

Synlett

Volumn 1996, Issue 7, 1996, Pages 645-646

  Mino, Takashi ^a   Takagi, Katsuyoshi ^a   Yamashita, Masakazu ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002533478     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5581     Document Type: Article

References (25)

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11. Mino, T; Yamashita, M. J. Org. Chem. 1996, 61, 1159.
12. Enders, D. in Asymmetric Synthesis Vol. 3, Morrison, J. D. (ed), Academic Press, Orlando, 1984, p. 275.
13. +, 20).
14. When LDA was used as a base, the yields of 4a-c were low.
15. We conducted the diastereoselective alkylation of 2 in several solvents such as THF-HMPA, DME, and ether, but THF gave the highest enantiomeric excesses of 4a.
16. Moore, J. S.; Stupp, S. I. J. Org. Chem. 1990, 55, 3374.
17. Smith, R.F.; Walker, L. E. J. Org. Chem. 1962, 27, 4372.
18. heptakis(2,3,6-tri-O-methyl)-b-cyclodextrin, 0.25 mm i.d. x 50 m.
19. Carlsen, P. H. J.; Katsuki, T.; Martin, V.S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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21. (b) Shaw, J. E.; Kunerth, D. C. J. Org. Chem. 1974, 39, 1968.
22. 2: C, 70.92; H, 6.45; N, 6.89. Found: C, 71.20; H, 6.66; N, 6.78.
23. 9
24. Cram, D. J.; Haberfield, P. J. Am. Chem. Soc., 1961, 83, 2363.
25. 21D = +6.48° (c 1.8, Ether) (79%e.e.).