Asymmetric C2−C3 Cyclopentannulation of the Indole Ring

• Published in: Journal of the American Chemical Society Vol. 131; no. 6; pp. 2096 - 2097
• Main Authors: Barluenga, José, Tudela, Eva, Ballesteros, Alfredo, Tomás, Miguel
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.02.2009; Amer Chemical Soc
• Subjects: Alkynes - chemistry; Chemistry; Chemistry, Multidisciplinary; Cyclopentanes - chemical synthesis; Indoles - chemical synthesis; Indoles - chemistry; Physical Sciences; Piperidines - chemical synthesis; Pyridines - chemistry; Science & Technology; Stereoisomerism; Tungsten - chemistry; TRANSITION-METAL-COMPLEXES; ONE-POT SYNTHESIS; CYCLOPENTADIENE ANNULATION; ENAMINES; TUNGSTEN; ORGANIC SYNTHESES; CARBENE COMPLEXES; CHROMIUM; C-H ACTIVATION; ACCESS

Chiral nonracemic alkynyl(alkoxy)carbene complexes of tungsten(0) undergo the [3 + 2] cyclization toward α-methylindoles and 1,6-dimethyl-1,2,3,4-tetrahydropyridine to provide 2,3-indoline-fused cyclopentenone and 2,3-piperidine-fused cyclopentenone skeletons, respectively, with very high enantiomer...