A general asymmetric route to enantio-enriched isoflavanes via an organocatalytic annulation of o-quinone methides and aldehydes. Issue 25 (20th June 2018)

• Record Type: Journal Article
• Authors: Zhang, Jian; Zhang, Shuangzhan; Yang, Huixin; Zhou, Ding; Yu, Xueting; Wang, Wei; Xie, Hexin
• Is Part Of: Tetrahedron letters. Volume 59:Issue 25(2018)
• Page Start: 2407
• Page End: 2411
• Publication Date: 2018-06-20
• Subjects: Isoflavanes -- Asymmetric -- Organocatalysis -- o-Quinone methide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.016
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A general asymmetric route to isoflavanes was developed. Five optically active natural isoflavanes were prepared. High synthetic efficiency. Abstract: Reported herein is a general approach to optically active isoflavanes based on a chiral amine-catalyzed [4 + 2] asymmetric annulation of o -quinone methides and aldehydes. A number of naturally occurring isoflavanes, including equol, sativan, isosativan, vestitol and medicarpin, as well as isoflavane analogues were readily prepared with good to excellent enantioselectivities.