Ytterbium triflate-catalyzed asymmetric hetero Diels-Alder cycloaddition of a 1-thiabuta-1,3-diene with a chiral N-acryloyloxazolidinone dienophile. Diastereoface control by solvents or achiral additives

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3231-3234

  Saito, Takao ^a   Kawamura, Mikako ^a   Nishimura, Jun Ichi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030901233     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00520-0     Document Type: Article

References (10)

1. Kobayashi, S. Synlett, 1994, 689.
2. (a) Kobayashi et al. and Takaki et al. recently reported the lanthanide triflate-catalyzed hetero Diels-Alder reaction of imines with carbodienes or alkenes to give cycloadducts such as pyridine and/or quinoline derivatives. Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis, 1995, 1195. Ishitani, H.; Kobayashi, S. Tetrahedron Lett., 1996, 37, 7357. Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis, 1995, 801.
3. (a) Kobayashi et al. and Takaki et al. recently reported the lanthanide triflate-catalyzed hetero Diels-Alder reaction of imines with carbodienes or alkenes to give cycloadducts such as pyridine and/or quinoline derivatives. Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis, 1995, 1195. Ishitani, H.; Kobayashi, S. Tetrahedron Lett., 1996, 37, 7357. Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis, 1995, 801.
4. (a) Kobayashi et al. and Takaki et al. recently reported the lanthanide triflate-catalyzed hetero Diels-Alder reaction of imines with carbodienes or alkenes to give cycloadducts such as pyridine and/or quinoline derivatives. Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis, 1995, 1195. Ishitani, H.; Kobayashi, S. Tetrahedron Lett., 1996, 37, 7357. Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis, 1995, 801.
5. (b) Mikami et al. described the lanthanide bis-trifylamide-catalyzed asymmetric oxa Diels-Alder reaction of glyoxylate with Danishefsky's diene. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett, 1995, 975.
6. (a) Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans, 1, 1991, 2281.
7. (b) Saito, T.; Fujii, H.; Hayashibe, S. ; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans, 1, 1996, 1897.
8. Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans, 1, 1994, 1351.
9. A 1,2-dithiin-type dimer was used as the precursor of 1. See literature in reference 2.
10. 2