87770-83-0Relevant articles and documents
Synthesis of 1-(5,6-dihydro-2H-thiopyran-2-yl)uracil by a Pummerer-type thioglycosylation reaction: the regioselectivity of allylic substitution
Yoshimura, Yuichi,Yamazaki, Yoshiko,Saito, Yukako,Takahata, Hiroki
, p. 9091 - 9102 (2009)
1-(5,6-Dihydro-2H-thiopyran-2-yl)uracil derivatives, a new 4′-thio-D4-nucleoside analogue, were synthesized by reacting 5,6-dihydro-2H-thiopyran sulfoxide and persilylated uracil in a Pummerer-type thioglycosylation reaction. The reaction of 5-alkyl subst
Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening
Milne, Kirsty,Henry, Martyn C.,Jamieson, Craig
supporting information, (2021/09/16)
We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-ind
Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy
Schrank, Cassandra L.,Danneman, Michael W.,Prebihalo, Emily A.,Anderson, Robert E.,Gibson, Tyler J.,Wuest, William M.,Mullins, Richard J.
supporting information, (2020/04/27)
In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (?)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidinone auxiliary.
Stereodivergent Hydroboration of Allenes
Nagashima, Yoshiyuki,Sasaki, Keiji,Suto, Takahiro,Sato, Takaaki,Chida, Noritaka
supporting information, p. 1024 - 1028 (2018/03/21)
Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.