Regio- and stereo-selective introduction of a bis(methoxycarbonyl)methyl group into the γ-position of the piperidine skeleton

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5715-5718

  Matsumura, Yoshihiro ^a   Yoshimoto, Yusuke ^a   Horikawa, Chikayo ^a   Maki, Toshihide ^a   Watanabe, Mitsuaki ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

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

EID: 0030570858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01208-7     Document Type: Article

References (9)

1. 1. For examples, a) Bosch, J.; Bonjoch, J. "Studies in Natural Products Chemistry", Vol. 1, p. 31, ed. by A.-u.-Rahman, Elsevier, New York, 1988.
2. b) Comins, D.L.; Baesky, M. F.; Hong, H. J.Am. Chem. Soc., 1992, 114, 10971-10972.
3. 2. a) Comins, D.L.; Killpac, M. O. J.Am.Chem.Soc. 1992, 114, 10972-10974.
4. b) Eynde, J.-J.V.; D'Orazio, P.; Mayence, A.; Maguestiau, A. Tetrahedron, 1992, 48, 1263-1268.
5. 3. Shono, T.; Terauchi, J.; Ohki, Y.; Matsumura, Y. Tetrahedron Lett., 1990, 31, 6385-6386.
6. 4. For examples, Barco, A.; Benetti, S.; Risi, C.D.; Pollini, G.P.; Romagnoli, R.; Spalluto, G; Zanirato, V. Tetrahedron, 1994, 50, 2583-2590.
7. 5. For example, Patai, S. ed. "The chemistry of carboxylic acids and esters" Interscience-Publishers, London, 1969.
8. 3, 500MHz) δ 1.76-1.85 (m, 1H) 2.43-2.49 (m, 1H), 2.80-2.85 (m, 1H), 3.30 (d, J=8.0Hz, 1H), 3.75 (s, 9H), 3.77 (s, 0.6 × 3H), 3.80 (s, 0.4 × 3H), 4.72 (d, J=8.5Hz, 0.6H), 4.79 (d, J=8.5Hz, 0.4H), 4.81 (dd, J=3.0, 5.1Hz, 0.6H), 4.93 (dd, J=3.0, 4.6Hz 0.4H), 6.83 (dd, J=1.6, 8.7Hz, 0.6H), 6.96 (dd, J=1.6, 8.5Hz, 0.4H).
9. 3, 500MHz) δ 1.74 (ddd, J=5.9, 11.9, 13.9Hz, 1H), 2.02 (ddd, J=1.1, 2.5, 13.7Hz, 1H), 3.10-3.15 (m, 1H), 3.33 (d, J=10.3Hz, 1H), 3.76 (s, 3H), 3.77 (s, 3H), 3.93 (d, J=7.7Hz, 1H), 3.95-4.00 (m, 1H), 4.6 (t, J=7.7Hz, 1H), 5.04 (ddd, J=1.4, 5.0, 8.0Hz, 1H) 6.71 (dd, J=1.6, 8.0Hz, 1H). The structure of 16 was estimated by the observation of NOEs between 2β proton (δ 3.95-4.00) and 3β proton (δ 2.02), and between 3α proton (δ 1.74) and 4α proton (δ 3.10-3.15).