Title:
CYCLOPROPANATION METHOD
Document Type and Number:
WIPO Patent Application WO/2019/035479
Kind Code:
A1
Abstract:
A cyclopropanation method includes reacting an alcohol, an ester, or an aldehyde with a sulfone in an organic solvent containing a base providing a counter cation to form a cyclopropane; and isolating the cyclopropane. When using the alcohol or ester, the organic solvent further contains a catalyst having an alcohol dehydrogenation activity.
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Inventors:
KHASKIN EUGENE (JP)
Application Number:
PCT/JP2018/030472
Publication Date:
February 21, 2019
Filing Date:
August 17, 2018
Export Citation:
Assignee:
OKINAWA INST SCIENCE & TECH SCHOOL CORP (JP)
International Classes:
C07C315/04; C07C317/22; C07C317/32
Other References:
BRANDT,A. ET AL.: "Synthesis of substituted tetrahydrofurans via intermolecular reactions of gamma-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes", TETRAHEDRON, vol. 66, no. 18, 2010, pages 3378 - 3385, XP055195793, DOI: doi:10.1016/j.tet.2010.02.006
SKARZEWSKI,J. ET AL.: "A new and efficient route to homochiral gamma-hydroxysulfoxides and gamma-hydroxysulfones", TETRAHEDRON : ASYMMETRY, vol. 13, no. 19, 4 October 2002 (2002-10-04), pages 2105 - 2111, XP004388545
T.TSUNODA ET AL.: "Arylmethyl phenyl sulfones, a new carbon nucleophile for Mitsunobu-type alkylation", TETRAHEDRON LETTERS, vol. 40, no. 41, 1999, pages 7359 - 7362, XP004178683, DOI: doi:10.1016/S0040-4039(99)01510-5
JIN,Z. ET AL.: "Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N-Heterocyclic-Carbene/Thiourea/Tertiary-Amin e Multicatalysis", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 52, no. 47, 18 November 2013 (2013-11-18), pages 12354 - 12358, XP055575739
JANKINS,T.C. ET AL.: "Three-Component [1 + 1 + 1] Cyclopropanation with Ruthenium(II", ORGANOMETALLICS, vol. 37, no. 15, 13 August 2018 (2018-08-13), pages 2609 - 2617, XP055575740
SKARZEWSKI,J. ET AL.: "A new and efficient route to homochiral gamma-hydroxysulfoxides and gamma-hydroxysulfones", TETRAHEDRON : ASYMMETRY, vol. 13, no. 19, 4 October 2002 (2002-10-04), pages 2105 - 2111, XP004388545
T.TSUNODA ET AL.: "Arylmethyl phenyl sulfones, a new carbon nucleophile for Mitsunobu-type alkylation", TETRAHEDRON LETTERS, vol. 40, no. 41, 1999, pages 7359 - 7362, XP004178683, DOI: doi:10.1016/S0040-4039(99)01510-5
JIN,Z. ET AL.: "Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N-Heterocyclic-Carbene/Thiourea/Tertiary-Amin e Multicatalysis", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 52, no. 47, 18 November 2013 (2013-11-18), pages 12354 - 12358, XP055575739
JANKINS,T.C. ET AL.: "Three-Component [1 + 1 + 1] Cyclopropanation with Ruthenium(II", ORGANOMETALLICS, vol. 37, no. 15, 13 August 2018 (2018-08-13), pages 2609 - 2617, XP055575740
Attorney, Agent or Firm:
KUZUWA, Kiyoshi (JP)
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