Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α‐Vinyl Appendage. Issue 11 (25th January 2018)

• Record Type: Journal Article
• Authors: Cui, Jin; Ohtsuki, Akimichi; Watanabe, Takumi; Kumagai, Naoya; Shibasaki, Masakatsu
• Is Part Of: Chemistry. Volume 24:Issue 11(2018)
• Page Start: 2598
• Page End: 2601
• Publication Date: 2018-01-25
• Subjects: aldol reactions -- asymmetric catalysis -- cooperative catalysis -- formal synthesis -- thioamide; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201800020
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The direct catalytic asymmetric aldol reaction is an emerging catalytic methodology that provides atom‐economical access to functionalized chiral building blocks. Thioamides are useful aldol donors due to their high‐fidelity chemoselective enolization and divergent post‐aldol transformations. Herein we describe the incorporation of an α‐vinyl appendage on a thioamide, which expands the utility of aldol adducts for natural product synthesis. This vinylated thioamide was not accommodated under the previously identified catalyst settings, but the newly developed catalytic conditions furnished aldol products containing the pendant vinyl group. Abstract : The direct catalytic asymmetric aldol reaction is an emerging catalytic methodology that provides atom‐economical access to functionalized chiral building blocks. Thioamides are useful aldol donors due to their high‐fidelity chemoselective enolization and divergent post‐aldol transformations. Herein we describe the incorporation of an α‐vinyl appendage on a thioamide, which expands the utility of aldol adducts for natural product synthesis. This vinylated thioamide was not accommodated under the previously identified catalyst settings, but the newly developed catalytic conditions furnished aldol products containing the pendant vinyl aldol reaction