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First Example of a Four‐Component Prins Cyclization Reaction: Diastereoselective Synthesis of Dithiocarbamate Derived Octahydro‐2 H ‐chromenes
Author(s) -
Sarmah Barnali,
Baishya Gakul,
Das Pranab J.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600539
Subject(s) - dithiocarbamate , prins reaction , reagent , chemistry , catalysis , carbon disulfide , organic chemistry , lewis acids and bases , brønsted–lowry acid–base theory , medicinal chemistry
A novel one‐pot sequential four‐component Prins cyclization reaction has been developed for the synthesis of dithiocarbamate derived octahydro‐2 H ‐chromenes directly from (‐)‐isopulegol by using fluoroboric acid etherate as an acid catalyst. Different dithiocarbamates generated in situ from different secondary amines and carbon disulfide participated well in this reaction. Among different Brønsted and Lewis acids catalysts screened for this protocol, fluoroboric acid etherate has been found to be the unique reagent which only drives the reaction in the forward direction affording the Prins cyclized products in moderate yields.