Enantioselective Construction of Spiro[chroman‐thiazolones]: Bifunctional Phosphonium Salt‐Catalyzed [2+4] Annulation between 5‐Alkenyl Thiazolones and ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides. Issue 5 (18th December 2019)

• Record Type: Journal Article
• Authors: Tan, Jian‐Ping; Zhang, Hongkui; Jiang, Zhiyu; Chen, Yuan; Ren, Xiaoyu; Jiang, Chunhui; Wang, Tianli
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 5(2020)
• Page Start: 1058
• Page End: 1063
• Publication Date: 2019-12-18
• Subjects: bifunctional phosphonium salt catalysis -- spiro-chroman-thiazolone -- [2+4] annulation -- 5-alkenyl thiazolones -- para-quinone methides.; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901413
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The enantioselective formal [2+4] annulation of 5‐alkenyl thiazolones with hydroxyl‐substituted para ‐quinone methides was disclosed by dipeptide‐based phosphonium salt catalysts. A wide range of functionalized spiro‐chroman‐thiazolone molecules bearing three contiguous 3° and/or 4° stereocenters were readily constructed in high yields with excellent stereoselectivities (>20:1 dr and up to >99.9% ee) under low catalyst loading and mild reaction conditions. The practicality and utility of this protocol were demonstrated by the scaled‐up preparation and elaborations of product. Abstract :