Diastereo- and enantioselective construction of chiral cyclopenta[b]indole framework via a catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols. Issue 9 (12th March 2018)

• Record Type: Journal Article
• Authors: Wu, Jia-Le; Wang, Jing-Yi; Wu, Ping; Wang, Jin-Rong; Mei, Guang-Jian; Shi, Feng
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 9(2018)
• Page Start: 1436
• Page End: 1445
• Publication Date: 2018-03-12
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00014j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The title reaction has been established in the presence of chiral phosphoric acids, which constructed chiral cyclopenta[ b ]indole frameworks in high stereoselectivities. Abstract : A catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols has been established in the presence of chiral phosphoric acids, which constructed chiral cyclopenta[ b ]indole frameworks in generally good yields (up to 90%), high diastereoselectivities (up to >95 : 5 dr) and excellent enantioselectivities (up to 96% ee). This reaction not only provides an easy access to chiral cyclopenta[ b ]indole scaffolds, but also advances the chemistry of indolylmethanols, especially catalytic asymmetric transformations of indolylmethanols.