Novel diastereoselective allene formation by an ene reaction of significantly twisted 1,3-dienes with singlet oxygen

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6461-6464

  Mori, Hajime ^a   Matsuo, Takafumi ^a   Yamashita, Kanako ^b   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b NONE

Author keywords

Allene formation; Diastereoselective; Singlet oxygen; Twisted diene

Indexed keywords

1,3 DIENE DERIVATIVE; ALLENE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHIRALITY; ISOLATION PROCEDURE; ORGANIC CHEMISTRY; OXYGEN AFFINITY; PHOTOSENSITIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033609757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01320-9     Document Type: Article

References (12)

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3. a)Mori, H.; Ikoma, K.; Isoe, S.; Kitaura, K.; Katsumura. S. Tetrahedron Lett., 1996, 37, 7771-7774.
4. b) Mori, H.; Ikoma, K.; Katsumura, S. Chem. Commun., 1997, 2243-2244.
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6. (a) Orfanopoulos, M.; Smonou, I.; Foote, C. S. J. Am. Chem. Soc. 1990, 112, 3607-3614.
7. (b) Elemes, Y.; Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1997, 38, 6437-6440, and references cited therein.
8. King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Comm., 1977, 683-684.
9. 3) δ 5.44(1H, d, J=1.7 Hz), 5.18(1H, s), 4.91(1H, s), 4.85(1H, d, J=3.9Hz),4.59(1H, dqd, J=3.7, 6.4, 1.7 Hz), 1.38-1.34(12H, m), 1.26(3H, d, J=6.4 Hz).
10. The geometries were optimized with MM2 forcefield using Macro Model verson 5.5 and 6.0.
11. 1H NMR, the hydroxy groups in 1a, e and f were observed at 3.2-4.2 ppm, while those of the 2 and 4 were 1.6-2.0 ppm. These differences would support the intramolecular hydrogen bonding in 1a,e and f.
12. The stable conformations of 1a,e and f were very similar, therefore, the pictorial conformation is represented by that of 1a.