Stereoselective and regioselective pinacol-type rearrangement of a fused bicyclic oxetanol scaffold
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201701214
Abstract: The Paterno-Buchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to unprecedented silyl ether derivatives of 6-oxabicyclo[3.2.0]heptan-1-ol. These bicyclic structures underwent selective reductive ring opening as well as acid-catalysed pinacol-type rearrangement with complete regioselectivity, accompanied by… read more here.
Keywords: pinacol type; stereoselective regioselective; type rearrangement;
An Electrocatalytic Newman-Kwart-type Rearrangement.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b03257
Abstract: An electrochemical approach toward rearrangement of O-aryl thiocarbamates to the corresponding S-aryl thiocarbamates is presented. The protocol requires only catalytic amounts of electric charge and allows for operation at room temperature. The electrolysis can be… read more here.
Keywords: electrocatalytic newman; type rearrangement; kwart type; newman kwart ... See more keywords
Enantioselective Total Synthesis of (+)-Stephadiamine through Bioinspired Aza-Benzilic Acid Type Rearrangement.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c00047
Abstract: We report the first enantioselective total syntheses of the hasubanan alkaloid (-)-metaphanine and the norhasubanan alkaloid (+)-stephadiamine. Key features of these syntheses include diastereoselective oxidative phenolic coupling reaction and subsequent regioselective intramolecular aza-Michael reaction, which… read more here.
Keywords: benzilic acid; type rearrangement; aza benzilic; enantioselective total ... See more keywords
Facile synthesis of methylthiomethyl esters through Pummerer-type rearrangement of carboxylic acids and DMSO under metal-free conditions
Sign Up to like & getrecommendations! Published in 2019 at "Synthetic Communications"
DOI: 10.1080/00397911.2019.1581894
Abstract: Abstract A green and cost-effective Pummerer-type rearrangement between readily accessible carboxylic acids and DMSO has been achieved under metal-free conditions in satisfactory to excellent yields. The transformation for the synthesis of valuable methylthiomethyl esters is… read more here.
Keywords: free conditions; type rearrangement; carboxylic acids; pummerer type ... See more keywords