Enantiodivergent synthesis of 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidines through tandem Michael-Henry reaction using L-serine as the chiral educt

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7599-7602

  Barco, Achille ^a   Benetti, Simonetta ^a   De Risi, Carmela ^b   Pollini, Gian P ^b   Romagnoli, Romeo ^a   Zanirato, Vinicio ^b  

^a Dipartimento di Chimica   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

CASTANOSPERMUM AUSTRALE;

EID: 0030583475     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01671-1     Document Type: Article

References (16)

1. 1. Fleet, G.W.J.; Wincester, B., Glycobiology, 1992, 2, 199-210.
2. 2. Harrison, T., Contemp. Org. Synth., 1995, 2, 209-224.
3. 3. Barco, A.; Benetti, S.; De Risi, C.; Pollini, G.P.; Romagnoli, R.; Zanirato, V., Tetrahedron Lett., 1994, 35, 9293-9296.
4. 4. Barco, A.; Benetti, S.; Pollini, G.P.; Spalluto, G., Synthesis, 1991, 479-480.
5. 5. For the utilization of L-serine as an important chiral building block in natural product synthesis: Meyers, A.I.; Schmidt, M.; McKennon, Synthesis, 1993, 250-262 and references quoted therein; Falorni, M.; Conti, S.; Giacomelli, G; Cossu, S.; Soccolini, F., Tetrahedron: Asymmetry, 1995, 6, 287-294; Novachek, K.A.; Meyers, A.I., Tetrahedron Lett., 1996, 37, 1743-1746.
6. For the utilization of L-serine as an important chiral building block in natural product synthesis: Meyers, A.I.; Schmidt, M.; McKennon, Synthesis, 1993, 250-262 and references quoted therein; Falorni, M.; Conti, S.; Giacomelli, G; Cossu, S.; Soccolini, F., Tetrahedron: Asymmetry, 1995, 6, 287-294; Novachek, K.A.; Meyers, A.I., Tetrahedron Lett., 1996, 37, 1743-1746.
7. For the utilization of L-serine as an important chiral building block in natural product synthesis: Meyers, A.I.; Schmidt, M.; McKennon, Synthesis, 1993, 250-262 and references quoted therein; Falorni, M.; Conti, S.; Giacomelli, G; Cossu, S.; Soccolini, F., Tetrahedron: Asymmetry, 1995, 6, 287-294; Novachek, K.A.; Meyers, A.I., Tetrahedron Lett., 1996, 37, 1743-1746.
8. 6. The conversion of L-serine into a variety of D-aminoacids has been originally described: Maurer, P.J.; Takahata, H.; Rapoport, H., J. Am. Chem. Soc., 1984, 106, 1095-1098.
9. 7. Barco, A.; Benetti, S.; Spalluto, G.; Casolari, A.; Pollini, G.P.; Zanirato, V., J. Org. Chem., 1992, 57, 6279-6286.
10. 2O), 3.5 (d, 1H, J=14), 3.6 (dd, 1H, J=12, J=4), 3.8 (m, 1H), 4.0 (d, 1H, J=14), 4.75 (dd, 1H, J=6, J=4), 4.9 (dt, 1H, J=7, J=4), 7.3 (m, 5H).
11. 3): δ 1.5-2 (m, 6H) ), 2.9 (m, 1H), 2.51 (sb, 2H, exchangeable with D2O), 3.4-3.6 (m, 4H, 3.7 (m, 2H), 3.85 (m, 2H), 3.9 (s,2H), 7.3 (m, 5H).
12. 10. Nash, R.J.; Bell, E.A.; Fleet, G.W.J.; Jones, R.H.; Williams, J.M., J. Chem. Soc. Chem. Commun., 1985, 738-740.
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16. Griffart-Brunet, D.; Langlois, N., Tetrahedron Lett., 1994, 35, 119-122; Herdeis, C.; Hubmann, H. P.; Lotter, H., Tetrahedron: Asymmetry, 1994, 5, 119-128.