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Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds.
J Org Chem. 2007 Apr 27; 72(9):3394-402.JO

Abstract

N-Aryl indoles with axially chiral N-C bonds were synthesized by stereoselective nucleophilic aromatic substitution reactions of planar chiral tricarbonyl(2,6-disubstituted-1-fluorobenzene)chromium complexes. The stereochemistry of the products is highly dependent on the position of the substituent in the indole. When indoles devoid of a substituent at the 2-position were used, N-aryl indole chromium complexes having anti orientation with respect to the tricarbonylchromium fragment were obtained diastereoselectively. In contrast, 2-substituted indoles gave the N-aryl indoles with syn orientation between the tricarbonylchromium fragment and the benzene ring of the indole. These results demonstrate that we have succeeded in synthesizing both enantiomers of N-aryl indoles utilizing an identical planar chiral arene chromium complex.

Authors+Show Affiliations

Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. kamikawa@c.s.osakafu-u.ac.jpNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17394356

Citation

Kamikawa, Ken, et al. "Stereoselective Synthesis of Both Enantiomers of N-aryl Indoles With Axially Chiral N-C Bonds." The Journal of Organic Chemistry, vol. 72, no. 9, 2007, pp. 3394-402.
Kamikawa K, Kinoshita S, Furusyo M, et al. Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds. J Org Chem. 2007;72(9):3394-402.
Kamikawa, K., Kinoshita, S., Furusyo, M., Takemoto, S., Matsuzaka, H., & Uemura, M. (2007). Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds. The Journal of Organic Chemistry, 72(9), 3394-402.
Kamikawa K, et al. Stereoselective Synthesis of Both Enantiomers of N-aryl Indoles With Axially Chiral N-C Bonds. J Org Chem. 2007 Apr 27;72(9):3394-402. PubMed PMID: 17394356.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds. AU - Kamikawa,Ken, AU - Kinoshita,Shunsuke, AU - Furusyo,Masaru, AU - Takemoto,Shin, AU - Matsuzaka,Hiroyuki, AU - Uemura,Motokazu, Y1 - 2007/03/30/ PY - 2007/3/31/pubmed PY - 2007/6/30/medline PY - 2007/3/31/entrez SP - 3394 EP - 402 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 9 N2 - N-Aryl indoles with axially chiral N-C bonds were synthesized by stereoselective nucleophilic aromatic substitution reactions of planar chiral tricarbonyl(2,6-disubstituted-1-fluorobenzene)chromium complexes. The stereochemistry of the products is highly dependent on the position of the substituent in the indole. When indoles devoid of a substituent at the 2-position were used, N-aryl indole chromium complexes having anti orientation with respect to the tricarbonylchromium fragment were obtained diastereoselectively. In contrast, 2-substituted indoles gave the N-aryl indoles with syn orientation between the tricarbonylchromium fragment and the benzene ring of the indole. These results demonstrate that we have succeeded in synthesizing both enantiomers of N-aryl indoles utilizing an identical planar chiral arene chromium complex. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17394356/Stereoselective_synthesis_of_both_enantiomers_of_N_aryl_indoles_with_axially_chiral_N_C_bonds_ DB - PRIME DP - Unbound Medicine ER -