Allyl as protective group for the acidic hydrogen of malonic ester

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2266-2267

  Yamazaki, Takanori ^a   Kasatkin, Aleksandr ^a,b   Kawanaka, Yasufumi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001741288     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600767     Document Type: Article

References (15)

1. (a) Cope, A. C.; Holmes, H. L.; House, H. O. In Organic Reactions; Adams, R., Ed.; John Wiley & Sons: New York, 1957; Vol. 9, p 107.
2. (b) House, H. O. Modern Synthetic Reactions; Benjamin: New York, 1972; p 492.
3. (c) Mathieu, J.; Weill-Raynal, J. Formation of C-C Bonds; Georg Thieme Publishers: Stuttgart, 1975; Vol. 2, p 12.
4. For some improvements to avoid dialkylation, see: Brandstrom, A.; Junggren, U. Tetrahedron Lett. 1972, 473. Bram. G.; Fillebeen-Khan, T. J. Chem. Soc., Chem. Commun. 1979, 522.
5. For some improvements to avoid dialkylation, see: Brandstrom, A.; Junggren, U. Tetrahedron Lett. 1972, 473. Bram. G.; Fillebeen-Khan, T. J. Chem. Soc., Chem. Commun. 1979, 522.
6. Protective Groups in Organic Chemistry; McOmie, J. F. W., Ed.; Plenum Press: New York, 1973 Greene, T. W.; Wuts, P G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991 Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991: Vol. 6, p 631.
7. Protective Groups in Organic Chemistry; McOmie, J. F. W., Ed.; Plenum Press: New York, 1973 Greene, T. W.; Wuts, P G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991 Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991: Vol. 6, p 631.
8. Protective Groups in Organic Chemistry; McOmie, J. F. W., Ed.; Plenum Press: New York, 1973 Greene, T. W.; Wuts, P G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991 Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991: Vol. 6, p 631.
9. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J Am. Chem. Soc. 1995, 117, 3881.
10. Reactions in which the malonate carbanion can be regarded as a leaving group have been reported as, for example. reactions of cyclopropane-1,1-dicarboxylates with nucleophiles; see: Danishefsky, S. Acc. Chem. Res. 1979, 22, 66. Hiyama, T.; Morizawa, Y.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 2151. Burgess, K. J. Org. Chem. 1987, 52, 2946. However, there is no precedent to use this type of reactions for protection of malonates.
11. Reactions in which the malonate carbanion can be regarded as a leaving group have been reported as, for example. reactions of cyclopropane-1,1-dicarboxylates with nucleophiles; see: Danishefsky, S. Acc. Chem. Res. 1979, 22, 66. Hiyama, T.; Morizawa, Y.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 2151. Burgess, K. J. Org. Chem. 1987, 52, 2946. However, there is no precedent to use this type of reactions for protection of malonates.
12. Reactions in which the malonate carbanion can be regarded as a leaving group have been reported as, for example. reactions of cyclopropane-1,1-dicarboxylates with nucleophiles; see: Danishefsky, S. Acc. Chem. Res. 1979, 22, 66. Hiyama, T.; Morizawa, Y.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 2151. Burgess, K. J. Org. Chem. 1987, 52, 2946. However, there is no precedent to use this type of reactions for protection of malonates.
13. It is known that cyclization of carbanions derived from (ω-haloalkyl)malonates to five-membered carbocycles is much faster than to six-membered ones, see: Knipe, A. C.; Stirling, C. J. M. J. Chem. Soc. B 1968, 67. Casadei, M. A.; Galli, C.; Mandolini, L. J. Am. Chem. Soc. 1984, 106, 1051.
14. It is known that cyclization of carbanions derived from (ω-haloalkyl)malonates to five-membered carbocycles is much faster than to six-membered ones, see: Knipe, A. C.; Stirling, C. J. M. J. Chem. Soc. B 1968, 67. Casadei, M. A.; Galli, C.; Mandolini, L. J. Am. Chem. Soc. 1984, 106, 1051.
15. Tsuji, J.; Minami, I.; Shimizu, I. Synthesis 1986, 623.