Mn-salen catalyzed asymmetric epoxidation of (±)-3-alkylindene: Reagent-dependent stereoselectivity

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4533-4536

  Noguchi, Yukiko ^a   Irie, Ryo ^a   Fukuda, Tsutomu ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; INDENE DERIVATIVE;

ARTICLE; CATALYST; EPOXIDATION; STEREOCHEMISTRY;

EID: 0030600176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00896-9     Document Type: Article

References (10)

1. 1. Katsuki, T.; Martin, V. S. Organic Reactions, 1996, 48, 1-299.
2. 2. For a recent review of Mn-salen catalyzed epoxidation, see: a) Katsuki, T. J. Synth. Org. Chem. Jpn. 1995, 53, 940-951.
3. b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
4. c) Jacobsen, E. N. In "Catalytic Asymmetric Synthesis" ed by I. Ojima, VCH publishers, Inc., New York, (1993), pp 159-202.
5. 3. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530.
6. 4. The intermediacy of the metallaoxetane intermediate in Mn-salen catalyzed epoxidation has also been proposed by calculation using macromodel/MM3: Norrby, P.-O.; Linde, C.; Åkermark, B. J. Am. Chem. Soc. 1995, 117, 11035-11036.
7. 5. Hamada, T.; Irie, R.; Katsuki, T. Synlett, 1994, 479-481.
8. 6. Vander Velde, S. L.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380-5381.
9. 7. Precise values could not be determined because the oxidation with 3 gave unidentified side products.
10. rel= 3) in the epoxidation of 3-methylindene. The ratio of trans-and cis-epoxides was 4:1 and their enantiomeric excesses were 87 and 92%, respectively, when 19% of the starting material were consumed.