Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones

Hitoshi Abe, Takenori Tsujino, Kenta Araki, Yasuo Takeuchi, Takashi Harayama

Research output: Contribution to journal › Article

9 Citations (Scopus)

Abstract

An efficient asymmetric synthesis of bicyclo[3.1.0]hexane derivatives was achieved. The three-step conversion of 6-hydroxytricyclo[3.2.1.02,7]octan-3-one 2, (derived from 3-oxatricyclo[3.3.1.02,4]nonan-7-one 1 through an asymmetric deprotonation reaction) led to 6 in optically active form. Alternatively, the asymmetric deprotonation reaction of meso-cyclic ketones 9a and 9b with several chiral lithium amide bases was examined to give silyl enol ether 12 and triflate 21 with high enantioselectivity. The absolute configuration of the triflate 21 was determined by investigation of the chemical relationship between 21 and 6.

Original languageEnglish
Pages (from-to)1519-1527
Number of pages9
JournalTetrahedron Asymmetry
Volume13
Issue number14
DOIs
Publication statusPublished - Aug 1 2002

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Deprotonation
Hexane
Ketones
Lithium
Amides
ketones
Ether
Derivatives
Enantioselectivity
amides
Ethers
ethers
lithium
synthesis
configurations
bicyclo(3.1.0)hexane

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones. / Abe, Hitoshi; Tsujino, Takenori; Araki, Kenta; Takeuchi, Yasuo; Harayama, Takashi.

In: Tetrahedron Asymmetry, Vol. 13, No. 14, 01.08.2002, p. 1519-1527.

Research output: Contribution to journal › Article

Abe, H, Tsujino, T, Araki, K, Takeuchi, Y & Harayama, T 2002, 'Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones', Tetrahedron Asymmetry, vol. 13, no. 14, pp. 1519-1527. https://doi.org/10.1016/S0957-4166(02)00405-6
Abe H, Tsujino T, Araki K, Takeuchi Y, Harayama T. Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones. Tetrahedron Asymmetry. 2002 Aug 1;13(14):1519-1527. https://doi.org/10.1016/S0957-4166(02)00405-6
Abe, Hitoshi ; Tsujino, Takenori ; Araki, Kenta ; Takeuchi, Yasuo ; Harayama, Takashi. / Enantioselective construction of bicyclo[3.1.0]hexane derivatives through asymmetric deprotonation of meso-cyclic ketones. In: Tetrahedron Asymmetry. 2002 ; Vol. 13, No. 14. pp. 1519-1527.
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