Catalytic Asymmetric [2+3] Cyclizations of Azlactones with Azonaphthalenes. (14th April 2018)

• Record Type: Journal Article
• Authors: Ma, Chun; Zhou, Jia‐Yu; Zhang, Yi‐Zhu; Mei, Guang‐Jian; Shi, Feng
• Is Part Of: Angewandte Chemie. Volume 130:Number 19(2018)
• Page Start: 5496
• Page End: 5500
• Publication Date: 2018-04-14
• Subjects: Asymmetrische Katalyse -- Azlactone -- Cyclisierungen -- Enantioselektivität -- Organokatalyse; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201801349
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The first catalytic asymmetric [2+3] cyclization of azlactones with azonaphthalenes has been established. This strategy allowed the synthesis of a variety of chiral isatin derivatives in generally good yields and excellent enantioselectivities (up to 99 % yield, 98 % ee ). The developed reaction has not only established a catalytic enantioselective [2+3] cyclization using azlactones as two‐carbon building blocks, but also enriches the chemistry of catalytic asymmetric cyclizations of azonaphthalenes. In addition, this protocol will provide a useful method for constructing enantioenriched 3, 3′‐disubstituted isatin‐type frameworks.