Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines.

Journal article

(figure represented) How to close a ring: An approach to catalytic asymmetric 6π electrocyclization leads to a highly enantioselective process that was used in the synthesis of chiral indolines (see scheme). Treatment of N-aryl imines under phase transfer conditions in the presence of N-benzyl cinchonidinium chloride generates a delocalized 2-aza-pentadienyl anion system that cyclizes in up to 99% yield and 98% ee. © 2009 Wiley-VCH Verlag GmbH and Co. KGaA.

Authors: Maciver, E; Thompson, S; Smith, M

• Publication status: Published
• Journal: Angewandte Chemie (International ed. in English)
• Volume: 48
• Issue: 52
• Pages: 9979-9982
• Publication date: 2009-01-01
• DOI: 10.1002/anie.200905169
• EISSN: 1521-3773
• ISSN: 1433-7851
• Language: English
• Keywords: Stereoisomerism; Cyclization; Imines; Catalysis; Indoles