Samarium(II) Iodide Promoted Ketone-Olefin Couplings Chelation-Controlled by (Alkoxycarbonyl)amino Groups

Synlett

Volumn 1996, Issue 4, 1996, Pages 373-376

  Kawatsura, M ^a   Dekura, F ^a   Shirahama, H ^a   Matsuda, F ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003141402     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5431     Document Type: Article

References (31)

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21. (a) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900.
22. (b) Kawatsura, M.; Hosaka, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 729.
23. 6]-promoted intermolecular pinacol coupling reactions chelation-controlled by the α-(alkoxycarbonyl)amino group. See: (a) Kondradi, A.W.; Pedersen, S.F. J. Org. Chem. 1990, 55, 4506. (b) Kondradi, A.W.; Pedersen, S.F. J. Org. Chem. 1992, 57, 28.
24. 6]-promoted intermolecular pinacol coupling reactions chelation-controlled by the α-(alkoxycarbonyl)amino group. See: (a) Kondradi, A.W.; Pedersen, S.F. J. Org. Chem. 1990, 55, 4506. (b) Kondradi, A.W.; Pedersen, S.F. J. Org. Chem. 1992, 57, 28.
25. The (±)-α-(benzyloxycarbonyl)amino ketones 1 and 3 were prepared from (±)-N-(benzyloxycarbonyl)-phenylalaninol and (±)-N-(benzyloxycarbonyl)- leucinol in 55% and 69% overall yields, respectively, by the sequence of (1) Swern oxidation, (2) the addition with methyl lithium, and (3) oxidation with pyridinium dichromate.
26. 3) δ 0.94, 0.97 (each 3H, d, J = 6.8 Hz), 1.04 (3H, d, J = 7.0 Hz), 1.17 (1H, ddd, J = 2.4, 10.1, 14.0 Hz), 1.26 (3H, s), 1.34 (1H, m), 1.55 (1H, ddd, J = 3.8, 11.2, 14.0 Hz), 1.63, 1.84 (each 1H, m), 1.92 (1H, ddq, J = 2.4, 10.5, 7.0 Hz), 2.06 (3H, s), 3.67 (1H, dd, J = 2.4, 11.0 Hz), 4.06 (1H, ddd, J = 6.3, 8.7, 11.2 Hz), 4.19 (1H, ddd, J = 4.1, 7.3, 11.2 Hz), 6.49 (1H, brs).
27. Sturino, C.F.; Fallis, A.G. J. Am. Chem. Soc. 1994, 116, 7447.
28. 10
29. 4a
30. 4, and filtered. Purification by preparative silica gel TLC (ethyl acetate / benzene, 30:70) afforded 2 (22.0 mg, 89%).
31. 10 but did affect the chemical yield of the γ-lactone 6. As the size of the alkyl group increased, the amount of the deoxygenated product (5-phenyl-2-pentanone) increased. In particular, use of tert-butyl crotonate produced a substantial decrease in product yield (5%).