References
- Magnus , P. D. 1977 . Tetrahedron , 33 : 2019
- Durst , T. 1979 . Comprehensive Organic Chemistry , Edited by: Jones , D. N. Vol. 3 , 171 – 195 . Oxford : Pergamon Press .
- Trost , B. M. and Ghadiri , M. R. 1986 . J. Am. Chem. Soc. , 108 : 1098
- Masuyama , Y. , Sato , H. and Kurusu , Y. 1985 . Tetrahedron Lett. , 26 : 67
- Masuyama , Y. , Yamazaki , H. , Toyoda , Y. and Kurusu , Y. 1985 . Synthesis , 964
- Monson , R. S. 1971 . Advanced Organic Synthesis, Methods and Techniques , 89 New York : Academic Press . Preparation of 2-carboethoxycycloalkanones: Material of 1a was prepared by Dieckmann condensation of diethyl adipate; see: Pinkney, P. S., Org. Synth. Coll. Vol. 2, 116. Materials of 1b-e were prepared by condensation of cycloalkanones with diethyl carbonate; see:
- Mandai , T. , Yanagi , T. , Araki , K. , Morisawa , Y. , Kawada , M. and Otera , D. 1984 . J. Am. Chem. Soc. , 106 : 3670 For isomerization of vinyl sulfone to allyl sulfone followed by elimination to olefin, see:
- The yields of crude products before purification. 1H NMR showed that these crude products are almost pure. The yields after purification were 4a (59%), 4b (22%), 4c (20%), and 8 (29–42%)
- Yield based on the consumed starting material is 75%
- Trost , B. M. and Vincent , J. E. 1980 . J. Am. Chem. Soc. , 102 : 5680
- All products obtained here exhibited satisfactory spectral and physical properties. 1H NMR (CCl4) of representative products: 4b; δ=1.20, 1.28 (2t, J=7Hz, 6H), 1.15–1.78 (m, 6H), 2.07–2.51 (m, 4H), 4.01, 4.12 (2q, J=7Hz, 4H), 5.33 (br.d, J=10Hz, 1H), 5.44 (br.d, J=16Hz, 1H), 6.58 (ddd, J=10,11,16Hz, 1H), and 7.30 (d, J=11Hz, 1H). 5a; δ=1.30 (t, J=7Hz, 3H), 1.89–2.23 (m, 2H), 2.37–2.62 (m, 4H), 4.19 (q, J=7Hz, 2H), 5.90 (d, J=12Hz, 1H), 6.50 (dd, J=6, 12Hz, 1H), and 7.27 (d, J=6Hz, 1H)