Journal
TETRAHEDRON
Volume 71, Issue 35, Pages 5952-5958Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.02.059
Keywords
1,5-C-H Insertion; Cyclopropylmagnesium carbenoid; 3-Azabicyclo[3.1.0]hexane; 1-Chlorocyclopropyl p-tolyl sulfoxide; Sulfoxide/magnesium exchange; Chiral auxiliary
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology KAKENHI [22590021]
- Japan Society for the Promotion of Science KAKENHI [25810030]
- TUS Grant for Research Promotion from the Tokyo University of Science
- Grants-in-Aid for Scientific Research [25810030] Funding Source: KAKEN
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A variety of 3-azabicylo[3.1.0]hexanes were synthesized via 1,5-C-H insertion of cyclopropylmagnesium carbenoids as a key step. 1-Chlorocyclopropyl p-tolyl sulfoxides with an N,N-disubstituted aminomethyl group on the cyclopropane ring were prepared from dichloromethyl p-tolyl sulfoxide, alpha,beta-unsaturated carboxylic acid esters, primary amines, and alkyl halides. Treatment of the sulfoxides with i-PrMgCl generated cyclopropylmagnesium carbenoids, which were inserted into an intramolecular C-H bond adjacent to a nitrogen atom to give 3-azabicyclo[3.1.0]hexanes in yields of up to 94%. The reactivity of the C-H bond toward the insertion increased in the order of NCH3, NCH2CH3, NCH2Ph, and NCH(CH3)(2). Optically active 3-azabicyclo[3.1.0]hexane was successfully synthesized using an S-chiral p-tolylsulfinyl group as a chiral auxiliary. (C) 2015 Elsevier Ltd. All rights reserved.
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