Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH4/AcOH and Heterogenous Hydrogenation Reactions
0
조회
0
다운로드
1
인용
0
참고문헌
키워드
초록
Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by NaBH4/AcOH and heterogenous hydrogenation were reported. Stereochemical assignment and diastereomeric ratios of the products were determined using 1H NMR and single crystal X-ray analyses. The steric factors of the C-5 substituents of the pyrrolidinone was shown to have an interesting influence on both the yield and diastereoselectivity of the reduced product.
Abstract
Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by NaBH4/AcOH and heterogenous hydrogenation were reported. Stereochemical assignment and diastereomeric ratios of the products were determined using 1H NMR and single crystal X-ray analyses. The steric factors of the C-5 substituents of the pyrrolidinone was shown to have an interesting influence on both the yield and diastereoselectivity of the reduced product.
참고문헌 (17)
- Royles, B. J. L., , Chem. Rev, 95, pp.1981~2001 (1995)
- Page, P. C. B., , Org. Lett, 5, pp.353~ (2003)
- Page, P. C. B., , Synlett, pp.1025~1027 (2003)
- Li, J., , J. Nat. Prod, 72, pp.2184~2187 (2009)
- Endo, A., , J. Am. Chem. Soc, 127, pp.8298~8299 (2005)
- Jourdan, F., , Synth. Commun, 33, pp.2235~2241 (2003)
- Mohammat, M. F., , Molecules, 14, pp.250~256 (2009)
- Bender, D. R., , J. Org. Chem, 40, pp.1264~1269 (1975)
- Dasse, O. A., , Lett. Drug. Des. Discov, 4, pp.263~271 (2007)
- Southwick, P. L., , J. Org. Chem, 21, pp.1087~1095 (1956)
- Mohammat, M. F., , ARKIVOC 2011, pp.ix 429~ix 438 (2011)
- Shaameri, Z., , J. Heterocyclic. Chem, 50, pp.320~332 (2013)
- Frage, C. A. M., , Synth. Commun, 25, pp.1133~ (1995)
- Metten, B., , Tetrahedron, 62, pp.6018~6028 (2006)
- Iglesias, M., , J. Org. Chem, 68, pp.2680~2688 (2003)
- Besson, M., , Top. Catal, 25, pp.43~61 (2003)
- Mansor, N. S., , Acta. Cryst. E, E69, pp.293~294 (2013)
