Computational insight into the mechanism and origin of high regioselectivity in the ring-opening cyclization of spirocyclopropanes with stabilized sulfonium ylides by the DFT
Sign Up to like & getrecommendations! Published in 2020 at "Journal of Molecular Modeling"
DOI: 10.1007/s00894-020-04522-1
Abstract: Chromanes with high bioactivity play an important role in nature, and cyclization reactions of cyclopropanes with sulfonium ylides to form chromane skeletons have attracted great attention of scientists. The mechanism as well as origins of… read more here.
Keywords: ring opening; regioselectivity; cyclization; opening cyclization ... See more keywords
Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
Sign Up to like & getrecommendations! Published in 2021 at "Chinese Chemical Letters"
DOI: 10.1016/j.cclet.2021.06.069
Abstract: Abstract A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as… read more here.
Keywords: sulfonium ylides; bond; alkylation arylation; non ylidic ... See more keywords
Mild and Diazo-Free Synthesis of Trifluoromethyl-Cyclopropanes Using Sulfonium Ylides.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b00557
Abstract: The synthesis of several 1,1-disubstituted trifluoromethyl-cyclopropanes (TFCPs), known as tert-butyl bioisosteres, has been achieved from the reaction between trifluoromethylalkenes and unstabilized sulfonium ylides in yields of ≤97%. This method offers practical access to this cyclopropyl… read more here.
Keywords: diazo free; trifluoromethyl cyclopropanes; sulfonium ylides; mild diazo ... See more keywords
Catalytic [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes: non-carbenoid Doyle-Kirmse reaction.
Sign Up to like & getrecommendations! Published in 2023 at "Chemical communications"
DOI: 10.1039/d3cc00160a
Abstract: The Sc(III)-catalyzed [2,3]-sigmatropic rearrangement of sulfonium ylides derived from azoalkenes has been established. Owing to the absence of a carbenoid intermediate, this protocol represents the first non-carbenoid variant of the Doyle-Kirmse reaction. Under mild conditions,… read more here.
Keywords: rearrangement sulfonium; non carbenoid; derived azoalkenes; ylides derived ... See more keywords