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Site‐Specific S‐Allylation of α‐Enolic Dithioesters with Morita‐Baylis‐Hillman Acetates at Room Temperature: Precursor for Thiopyrans
Author(s) -
Soni Sonam,
Koley Suvajit,
Ansari Monish A.,
Singh Maya Shankar
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900580
Subject(s) - chemistry , allylic rearrangement , tsuji–trost reaction , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.