Application of Homophthalic Anhydrides as 2C Building Blocks in Catalytic Asymmetric Cyclizations of ortho‐Quinone Methides: Diastereo‐ and Enantioselective Construction of Dihydrocoumarin Frameworks. Issue 6 (29th December 2017)

• Record Type: Journal Article
• Authors: Zhang, Ting; Ma, Chun; Zhou, Jia‐Yu; Mei, Guang‐Jian; Shi, Feng
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 6(2018)
• Page Start: 1128
• Page End: 1137
• Publication Date: 2017-12-29
• Subjects: asymmetric organocatalysis -- cyclization -- dihydrocoumarin -- enantioselectivity -- ortho-quinone methides -- tandem reaction; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701333
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A catalytic asymmetric [4+2] cyclization of ortho ‐quinone methides with homophthalic anhydrides in the presence of chiral squaramide‐tertiary amine has been established. This method provides dihydrocoumarin frameworks in excellent diastereoselectivities (all >95:5 dr) and high enantioselectivities (81%–98% ee). This reaction represents the first application of homophthalic anhydrides as 2C building blocks in catalytic asymmetric cyclizations. In addition, this approach not only provides a useful method for constructing enantioenriched dihydrocoumarin frameworks but also advances the chemistry of catalytic asymmetric cyclizations of ortho ‐quinone methides. Abstract :