81369-90-6Relevant academic research and scientific papers
Diterpenoid alkaloid lappaconine derivative catalyzed asymmetric α-hydroxylation of β-dicarbonyl compounds with hydrogen peroxide
Li, Zhi,Lian, Mingming,Yang, Fan,Meng, Qingwei,Gao, Zhanxian
supporting information, p. 3491 - 3495 (2014/06/09)
A new framework derived from the commercially available diterpenoid alkaloid lappaconitine was evaluated as a Bronsted base catalyst for the enantioselective α-hydroxylation of β-dicarbonyl compounds by using 30% hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding α-hydroxy-β- oxo esters, α-hydroxy-β-oxo amides and (-)-kjellmanianone with up to 98% yield and 92% ee. Copyright
ENANTIOSELECTIVE SYNTHESIS OF (+)-KJELLMANIANONE
Chen, Bang-Chi,Weismiller, Michael C.,Davis, Franklin A.,Boschelli, Diane,Empfield, James R.,Smith, Amos B.
, p. 173 - 182 (2007/10/02)
An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (1) has been achieved.The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester 2 with the new, enatiomerically pure N-sulfonyloxaziridine 7b, affording 1 in 68.5percent ee (60percent yield).Possible transition state structures for the asymmetric oxidation are evaluated.
