Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet-Spengler-Type Reactions.
| Autor: | Hansen CL; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark., Ohm RG; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark., Olsen LB; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark., Ascic E; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark., Tanner D; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark., Nielsen TE; Department of Chemistry, Technical University of Denmark , DK-2800 Kgs Lyngby, Denmark.; Singapore Centre on Environmental Life Sciences Engineering, Nanyang Technological University , Singapore 637551, Singapore. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2016 Dec 02; Vol. 18 (23), pp. 5990-5993. Date of Electronic Publication: 2016 Nov 16. |
| DOI: | 10.1021/acs.orglett.6b02718 |
| Abstrakt: | A synthetic strategy for the synthesis of chiral tetrahydrocarbazoles (THCAs) has been developed. The strategy relies on two types of 6-exo-trig cyclization of 3-substituted indole substrates. Enantioselective domino Friedel-Crafts-type reactions leading to THCAs can be catalyzed by chiral phosphoric acid derivatives (with up to >99% ee), and the first examples of exocyclic Pictet-Spengler reactions to form THCAs are reported. |
| Databáze: | MEDLINE |
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