76291-90-2Relevant articles and documents
Enantioselective protecting-group-free synthesis of (+)-9,10-dihydroecklonialactone B
Yassen, Asmaa Said Ali,Ishihara, Jun,Hatakeyama, Susumi
, p. 59 - 63 (2017/02/26)
An enantioselective protecting-group-free route to ecklonialactones, C-18 oxylipins isolated from the brown algae, was demonstrated by the synthesis of (+)-dihydroecklonialactone B from (E)-ethyl hex-3-enoate in 17 steps.
Copper catalyzed asymmetric synthesis of chiral allylic esters
Geurts, Koen,Fletcher, Stephen P.,Feringa, Ben L.
, p. 15572 - 15573 (2007/10/03)
The complex derived from Taniaphos ligand 4 and CuBr?Me2S catalyzes the asymmetric addition of Grignard reagents to 3-bromopropenyl esters 1 to provide allylic esters 2 in high yields and high chemio-, regio-, and enantioselectivities. The work demonstrates that allylic asymmetric alkylation (AAA) can be done on substrates bearing a heteroatom at the γ-position. The method is a practical route to chiral, nonracemic allylic alcohols. The use of functionalized substrates 1 or Grignard reagents leads to more complex products 2, which can be further manipulated as demonstrated in conversion to (S)-5-ethyl-2(5H)-furanone 6 and (S)-benzoic acid-cyclopent-2-enyl ester 7. Copyright
Kinetic resolution of racemic lactones by conjugate additions of allylic organolithium species: Direct formation of three contiguous centers with high diastereo- and enantioselectivities
Lim, Sung H.,Beak, Peter
, p. 2657 - 2660 (2007/10/03)
(Matrix presented) Kinetic resolution of racemic α,β-unsaturated lactones by the organolithium species produced from asymmetric lithiation of N-Boc-N-(p-methoxyphenyl)cinnamylamine provides conjugate addition products with three contiguous stereogenic centers in yields of 62-77% with diastereomeric ratios from 75:25 to >99:1 and enantiomeric ratios for the major diastereomers from 94:6 to 98:2.
