Construction of contiguous chiral tertiary carbon centers by enantioselective Michael reaction of ketone lithium enolates using a chiral amine ligand

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3531-3534

  Yasuda, Kosuke ^a   Shindo, Mitsum ^b   Koga, Kenji ^c  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL PHENYL KETONE; KETONE;

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

EID: 0030921406     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00695-3     Document Type: Article

References (20)

1. a) Cram, D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625-628.
2. b) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100.
3. c)Sawamura, M.; Hamashima, H.; Shinoto, H.; Ito, Y. Tetrahedron Lett. 1995, 36, 6479-6482.
4. d)Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
5. e) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
6. f) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924, and references cited therein.
7. Tin(II) enolate: Yura, T.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1988, 1021-1024; silyl ketene acetal: Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363-1364; enamine: Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122-2127.
8. Tin(II) enolate: Yura, T.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1988, 1021-1024; silyl ketene acetal: Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363-1364; enamine: Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122-2127.
9. Tin(II) enolate: Yura, T.; Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1988, 1021-1024; silyl ketene acetal: Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363-1364; enamine: Hayashi, Y.; Otaka, K.; Saito, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1991, 64, 2122-2127.
10. A cyclic ketone (cyclohexanone) was used as the Michael donor in the diastereo-and enantioselective Michael reaction of β-nitro-olefins. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
11. In addition to ref. 3, only one enantioselective Michael reaction using a ketone as the Michael donor has been repoted. Quaternary Cinchona alkaloids were used as phase-transfer catalysts for the Michael reaction of 6,7-dichloro-5-methoxy-2-propylindanone and methyl vinyl ketone. Conn, R. S. E.; Lovell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710-4711.
12. Shirai, R.; Aoki, K.; Sato, D.; Kim, H.-D.; Murakata, M.; Yasukata, T.; Koga, K. Chem. Pharm. Bull. 1994, 42, 690-693.
13. Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1996, 37, 6343-6346.
14. The relative and absolute configurations of all the major products (anti-4a-f) were confirmed by chemical correlations and/or X-ray crystallographical analyses. The details other than those of anti-4d will be reported elsewhere.
15. 3: Reddy, G. B.; Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1991, 32, 521-524; Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
16. 3: Reddy, G. B.; Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1991, 32, 521-524; Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
17. b) Selective reduction of the carboxylic acid with borane-dimethyl sulfide complex: Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710-6716.
18. Mori, K.; Ueda, H. Tetrahedron 1982, 38, 1227-1233.
19. 13C-NMR spectra of both the cis-and trans-isomers in dl-forms are reported. Wei, S.-Y.; Tomooka, K.; Nakai, T. Tetrahedron 1993, 49, 1025-1042.
20. HPLC conditions: CHIRALPAK AD®, hexane-isopropanol (9:1), 0.5 mL/min, UV 254 nm. Under these conditions, all the four stereoisomers were detected as four separated peaks.