Regioselective Diels–Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes

• Published in: Tetrahedron letters Vol. 50; no. 1; pp. 63 - 65
• Main Authors: Brown, Neil, Luo, Diheng, Vander Velde, David, Yang, Shaorong, Brassfield, Allen, Buszek, Keith R.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.01.2009; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; TRIFLATE; 2-SUBSTITUTED FURANS; (+/-)-CIS-TRIKENTRIN-B; PHENOLS; TELEOCIDIN; DERIVATIVES; BENZYNE

The regioselectivity of Diels–Alder cycloadditions of indole arynes (indolynes) at all three benzenoid positions was examined. The 6,7-indolyne displayed virtually complete preference for the more sterically congested cycloaddduct, and undergoes an acid-catalyzed rearrangement to afford annulated en...