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Chemistry Letters

Volumn , Issue 9, 2002, Pages 900-901

Asymmetric Diels-Alder reactions catalyzed by chiral Ni(II)-binaphthyldiimine complexes

(3) Suga, Hiroyuki a Kakehi, Akikazu a Mitsuda, Masashi a

a SHINSHU UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; LEWIS ACID; NICKEL; NICKEL COMPLEX; NICKEL N,N' BIS(2 QUINOLYLMETHYLENE) 1,1' BINAPHTHYL 2,2' DIAMINE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0037026811 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2002.900 Document Type: Article

Times cited : (20)

References (9)

1
- 84962105974
- O. Diels and K. Alder, Justus Liebigs Ann. Chem., 460, 98 (1928).
- (1928) Justus Liebigs Ann. Chem. , vol.460 , pp. 98
- Diels, O.¹ Alder, K.²

2
- 0000097153
- ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, New York, Chap. 33.1, and references therein
- For recent reviews of enantioselective Diels-Alder reactions, see: D. A. Evans, J. S. Johnson, in "Comprehensive Asymmetric Catalysts," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, New York (1999), Vol. 3, Chap. 33.1, p 1177 and references therein.
- (1999) Comprehensive Asymmetric Catalysts , vol.3 , pp. 1177
- Evans, D.A.¹ Johnson, J.S.²

3
- 0001000348
- H. Suga, T. Fudo, and T. Ibata, Synlett, 1998, 933.
- Synlett , vol.1998 , pp. 933
- Suga, H.¹ Fudo, T.² Ibata, T.³

4
- 0011851502
- unpublished results
- H. Suga, A. Kakehi, S. Ito, T. Ibata, T. Fudo, Y. Watanabe, and Y. Kinoshita, unpublished results.
- Suga, H.¹ Kakehi, A.² Ito, S.³ Ibata, T.⁴ Fudo, T.⁵ Watanabe, Y.⁶ Kinoshita, Y.⁷

5
- 0035842869
- Recently, Shi reported the Cu(I)-BINIM-catalyzed aziridination reactions: M. Shi, C.-J. Wang, and A. S. Chan, Tetrahedron: Asymmetry, 12, 3105 (2001).
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3105
- Shi, M.¹ Wang, C.-J.² Chan, A.S.³

6
- 0011905302
- submitted for publication
- H. Suga, A. Kakehi, S. Ito, and H. Sugimoto, submitted for publication.
- Suga, H.¹ Kakehi, A.² Ito, S.³ Sugimoto, H.⁴

7
- 0032495777
- and references therein
- Ni(II)-Catalyzed asymmetric Diels-Alder reactions using Chiral 4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) were reported by Kanemasa: S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, and D. P. Curran, J. Am. Chem. Soc., 120, 3074 (1998), and references therein.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 3074
- Kanemasa, S.¹ Oderaotoshi, Y.² Sakaguchi, S.³ Yamamoto, H.⁴ Tanaka, J.⁵ Wada, E.⁶ Curran, D.P.⁷

8
- 0011811639
- note
- 2 (1.0mL). After cooling the mixture to -40°C, the reaction mixture was allowed to react with cyclopentadiene (0.331 g, 5.0 mmol) for 17 h. Usual workup and chromatographic procedures afforded the cycloadducts (99mg, 94%). The endo:exo ratio and enantiomeric purity were evaluated using HPLC (Daicel Chiralpak AD).

9
- 0011851772
- note
- Geometry optimizations were performed using PC Spartan Pro (Version 1.0.5) program.

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