Allylation of p-ketoaldehydes and functionalized imines by diallyltin dibromide: Formation of skipped and conjugated dienes

References

• Yamamoto , Y. and Asao , N. 1993 . Chem. Rev. , 93 : 2207 b) Auge, J. and Bourdeaux, G. J. Organomet. Chem. 1989, 377 205; c) Takuwa, A., Shigi, J. and Nishigaichi, V. Tetrahedron Lett. 1993, 34 3457; d) Carey, J. S. and Thomas, J. J. Chem. Soc., Chem. Commun. 1994, 283
   Web of Science ®Google Scholar
• Yanagisawa , A. , Inoue , H. , Morodome , M. and Yamamoto , H. 1993 . J. Am. Chem. Soc. , 115 : 10356
   Google Scholar
• Boga , C. , Savoia , D. , Tagliavini , E. , Trombini , C. and Umanironchi , A. 1988 . J. Organomet. Chem. , 353 : 177
   Google Scholar
• Sisido , K. and Takeda , Y. 1961 . J. Org. Chem. , 26 : 2307
   Google Scholar
• Bokadia , M. M. and Deshpande , S. S. 1949 . J. Ind. Chem. Soc. , 26 : 455 b) Bokadia, M. M.Chem. Abstr. 1953. 47 12127d
   Google Scholar
• Hagen , G. and Moyr , H. 1991 . J. Am. Chem. Soc. , 113 : 4954
   Google Scholar
• Petrier , C. , Einhorn , J. and Luche , J. L. 1985 . Tetrahedron Lett. , 26 : 1449 b) Uneyama, K., Nanbu, H. and Trii, S. J. Organomet. Chem. 1987, 322 177; c) Schmid, W. and Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 6674
   Web of Science ®Google Scholar
• Hulst , R. , de Vries , N. K. and Feringa , B. L. 1994 . Tetrahedr. Asymm. , 5 : 699
   Web of Science ®Google Scholar
• In the reaction of the β-ketoaldehyde derived from acenapthenequinone also a skipped diene is formed [′H NMR: 3.45 (t(complex), 2H. =C-CH2-C=), 5.10–5.25 (m, 2H, CH=CH2). 5.61–6.05 (m, 1H, CU=CH2), 6.98 (t, 1H. CH=CAr)]; however we were not able to purify it satisfactorily
   Google Scholar
• Perrin , D. D. , Armarego , W. L. F. and Perrin , D. R. 1986 . Purification of Laboratory Chemicals , Oxford : Pergamon .
   Google Scholar
• Mayer , R. , Nitzschke , M. and Jentzsch , J. 1963 . Angew. Chem. Int. Ed. Engl. , 2 : 370
   Google Scholar
• Nakazawa , K. , Matsura , S. and Kusuda , K. 1954 . J. Pharm. Soc. Jpn. , 74 : 495 Chem. Abstr. 1955, 49 8182
   Google Scholar
• Buck , J. S. and Ide , W. S. 1930 . J. Am. Chem. Soc. , 52 : 4107
   Google Scholar
• Bishop , A. W. , Claisen , L. and Sinclair , W. 1894 . Liebigs. Ann. Chem. , 257 : 314
   Google Scholar
• Roch , L. M. 1961 . Annal de Chem (Paris). , 6 : 1
   Google Scholar
• Wislicenus , W. and Ruthing , A. 1911 . Liebigs. Ann. Chem. , 379 : 229
   Google Scholar
• Huttel , R. , Franke , K. , Martin , H. and Riedl , J. 1960 . Chem. Ber. , 93 : 1433
   Google Scholar
• Data for the new β-ketoaldehydes: 2c (From (R)-(+)-pulegone). Yield 40% (purity 85%). Liquid. 1H NMR: 1.09 (d, 1=6.8 Hz, 3H, CH3), 1.30–1.80 (m, 4H, 2CH2), 1–87, 2.24 (2s, 6H, 2CH3-C=C), 2.30 (m, 1H, CHCH3), 8.41 (s, 1H, CHOH), 15.58 (br, 1H, OH). 13C NMR (major peaks only): 21.0 (CH3CH), 24.3, 24.9 (2 CH2), 29.3, 30.3 (2CH3-C=C), 49.6 (CHCH3), 114.5, 115.6, 126.0 (C=C), 148.2 (CHOH), 181.8 (C=O)
   Google Scholar
• (From 4-methylbenzyl 4-methylphenyl ketone). Yield 44%, m.p. 115°C. 1H NMR: 2.31, 2.34 (2s, 6H, 2CH3), 6.95–7.38 (m, 8H, Ar-H), 8.59 (d, J = 5 Hz, 1H, CHOH), 15.97 (d, 1=5 Hz, 1H, OH). 13C NMR: 21.2, 21.6 (2CH3), 115.8, 128.7, 129.4, 129.5, 130.1, 136.9, 142.0 (C(Ar) + C=CHOH), 184.4 (CHOH)
   Google Scholar