Site‐Specific S‐Allylation of α‐Enolic Dithioesters with Morita‐Baylis‐Hillman Acetates at Room Temperature: Precursor for Thiopyrans. Issue 17 (22nd July 2019)

• Record Type: Journal Article
• Authors: Soni, Sonam; Koley, Suvajit; Ansari, Monish A.; Singh, Maya Shankar
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 17(2019)
• Page Start: 4091
• Page End: 4105
• Publication Date: 2019-07-22
• Subjects: MBH acetate -- α-Enolic dithioesters -- Thiopyrans -- Regioselectivity -- Allylation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900580
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An efficient one‐pot allylic alkylation of α‐enolic dithioesters (DTEs) with Morita‐Baylis‐Hillman (MBH) acetates has been devised in ethanol at room temperature. The reaction being site‐selective provided S‐allylated product exclusively with trace amount of C‐allylated one. Remarkably, some of the S‐allylated product undergoes [3, 3]‐sigmatropic rearrangement to C‐allylated one under ethanol reflux. The typical feature of this protocol is the isolation of S‐allylated α‐oxoketene dithioacetals, a trisubstituted olefin, which have been further exploited toward the synthesis of thiopyrans. Abstract :